102 results match your criteria oxazolidin-2-ones

Chemodivergent Synthesis of Oxazolidin-2-ones via Cu-Catalyzed Carboxyl Transfer Annulation of Propiolic Acids with Amines.

J Org Chem 2021 12 2;86(23):16940-16947. Epub 2021 Nov 2.

College of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai 201620, China.

Carboxylic acids are widely found in natural products and bioactive molecules and have served as raw material compounds in industry. We now report the first example of copper(I)-catalyzed carboxyl transfer annulation of propiolic acids with amines, thereby chemodivergently constructing the oxazolidine-2-ones. In this reaction, two kinds of key propargyamine intermediates were formed through sequential CuI/NBS-catalyzed oxidative deamination/decarboxylative alkynylation or CuI-catalyzed decarboxylative hydroamination/alkynylation. Read More

View Article and Full-Text PDF
December 2021

A Giese reaction for electron-rich alkenes.

Chem Sci 2020 Dec 17;12(6):2225-2230. Epub 2020 Dec 17.

Department of Chemistry and Biochemistry, University of Bern Freiestrasse 3 CH-3012 Bern Switzerland

A general method for the hydroalkylation of electron-rich terminal and non-terminal alkenes such as enol esters, alkenyl sulfides, enol ethers, silyl enol ethers, enamides and enecarbamates has been developed. The reactions are carried out at room temperature under air initiation in the presence of triethylborane acting as a chain transfer reagent and 4--butylcatechol (TBC) as a source of hydrogen atom. The efficacy of the reaction is best explained by very favorable polar effects supporting the chain process and minimizing undesired polar reactions. Read More

View Article and Full-Text PDF
December 2020

Non-precious metal carbamates as catalysts for the aziridine/CO coupling reaction under mild conditions.

Dalton Trans 2021 Apr;50(15):5351-5359

Dipartimento di Chimica e Chimica Industriale, University of Pisa, Via G. Moruzzi 13, I-56124 Pisa, Italy. and CIRCC, via Celso Ulpiani 27, I-70126 Bari, Italy.

The catalytic potential of a large series of easily available metal carbamates (based on thirteen different non-precious metal elements) was explored for the first time in the coupling reaction between 2-aryl-aziridines and carbon dioxide, working under solventless and ambient conditions and using tetraalkylammonium halides as co-catalysts. The straightforward synthesis of novel [NbCl3(O2CNEt2)2], NbCl, and [NbBr3(O2CNEt2)2], NbBr, is reported. The niobium complex NbCl, in combination with NBu4I, emerged as the best catalyst of the overall series to convert aziridines with small N-alkyl substituents into the corresponding 5-aryl-oxazolidin-2-ones. Read More

View Article and Full-Text PDF

Stereoselective Synthesis of Oxazolidin-2-Ones via an Asymmetric Aldol/Curtius Reaction: Concise Total Synthesis of (-)-Cytoxazone.

Molecules 2021 Jan 23;26(3). Epub 2021 Jan 23.

Department of Chemistry, The Catholic University of Korea, Bucheon 14662, Korea.

Herein, we are reporting an efficient approach toward the synthesis of 4,5-disubstituted oxazolidin-2-one scaffolds. The developed approach is based on a combination of an asymmetric aldol and a modified Curtius protocol, which uses an effective intramolecular ring closure to rapidly access a range of oxazolidin-2-one building blocks. This strategy also permits a straightforward and concise asymmetric total synthesis of (-)-cytoxazone. Read More

View Article and Full-Text PDF
January 2021

Cu(II)-Catalyzed Phosphonocarboxylative Cyclization Reaction of Propargylic Amines and Phosphine Oxide with CO.

J Org Chem 2020 11 29;85(21):14109-14120. Epub 2020 Oct 29.

State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.

Compounds bearing organophosphorus motifs and 2-oxazolidinone have found numerous applications in pharmaceutical chemistry, homogeneous catalysis, and organic materials. Here, we describe an efficient and selective protocol for straightforward access to a series of 5-((diarylphosphoryl)methyl)oxazolidin-2-ones via the copper-catalyzed difunctionalization of the C≡C bond of propargylic amines with CO and phosphine oxide. Notably, copper catalysis is a sustainable and benign catalytic mode. Read More

View Article and Full-Text PDF
November 2020

Pyranoid Spirosugars as Enzyme Inhibitors.

Curr Org Synth 2020 Sep 24. Epub 2020 Sep 24.

Department of Biotechnology and Bioscience, University of Milano-Bicocca, Milan. Italy.

Background: Pyranoid spirofused sugar derivatives represent a class of compounds with a significant impact in the literature. Under the structural point of view, the rigidity inferred by the spirofused entity has made these compound object of interest mainly as enzymatic inhibitors, in particular of carbohydrate processing enzymes among which glycogen phosphorylase and sodium glucose co-transporter 2, important target enzymes for diverse pathological states. Most of the developed compounds present the spirofused entity at the C1 position of the sugar moiety, nevertheless spirofused entities can also be found at other sugar ring positions. Read More

View Article and Full-Text PDF
September 2020

Regioselectivity of the trifluoroethanol-promoted intramolecular -Boc-epoxide cyclization towards 1,3-oxazolidin-2-ones and 1,3-oxazinan-2-ones.

Org Biomol Chem 2020 Sep;18(37):7401-7413

Department of Chemical Sciences, Tezpur University, Napaam, Tezpur, Assam 784028, India.

The intramolecular N-Boc-epoxide cyclization leading to the formation of 1,3-oxazolidin-2-one and 1,3-oxazinan-2-one derivatives has scarcely been reported in the literature. More specifically, the intramolecular cyclization of N-Boc aniline-tethered 2,3-disubstitued epoxides has never been disclosed. Herein, we demonstrate that this reaction could proceed in a diastereoselective fashion in refluxing trifluoroethanol, in the absence of any external promoter or catalyst. Read More

View Article and Full-Text PDF
September 2020

A One-Pot Iodo-Cyclization/Transition Metal-Catalyzed Cross-Coupling Sequence: Synthesis of Substituted Oxazolidin-2-ones from -Boc-allylamines.

Org Lett 2020 May 28;22(10):3870-3874. Epub 2020 Apr 28.

Molecular, Macromolecular Chemistry and Materials, ESPCI Paris, PSL University, CNRS, 75005 Paris, France.

A one-pot iodo-cyclization/transition metal-catalyzed cross-coupling sequence is reported to access various C5-functionalized oxazolidin-2-ones from unsaturated Boc-allylamines. Depending on the Grignard reagents used for the cross-coupling, e.g. Read More

View Article and Full-Text PDF

The Synthesis of Functionalized 3-Aryl- and 3-Heteroaryloxazolidin-2-ones and Tetrahydro-3-aryl-1,3-oxazin-2-ones via the Iodocyclocarbamation Reaction: Access to Privileged Chemical Structures and Scope and Limitations of the Method.

J Org Chem 2020 05 5;85(10):6323-6337. Epub 2020 May 5.

Department of Chemistry and Biochemistry, Calvin University, 1726 Knollcrest Circle SE, Grand Rapids, Michigan 49546, United States.

3-Aryl- and 3-heteroaryloxazolidin-2-ones, by virtue of the diverse pharmacologic activities exhibited by them after subtle changes to their appended substituents, are becoming increasingly important and should be considered privileged chemical structures. The iodocyclocarbamation reaction has been extensively used to make many 3alkyl-5-(halomethyl)oxazolidin-2-ones, but the corresponding aromatic congeners have been relatively underexplored. We suggest that racemic 3-aryl- and 3-heteroaryl-5-(iodomethyl)oxazolidin-2-ones, readily prepared by the iodocyclocarbamation reaction of N-allylated aryl or heteroaryl carbamates, may be useful intermediates for the rapid preparation of potential lead compounds with biological activity. Read More

View Article and Full-Text PDF

5-(Carbamoylmethylene)-oxazolidin-2-ones as a Promising Class of Heterocycles Inducing Apoptosis Triggered by Increased ROS Levels and Mitochondrial Dysfunction in Breast and Cervical Cancer.

Biomedicines 2020 Feb 18;8(2). Epub 2020 Feb 18.

Department of Pharmacy, Health and Nutritional Sciences, University of Calabria, Via P. Bucci, 87036 Rende (CS), Italy.

Oxazolidinones are antibiotics that inhibit protein synthesis by binding the 50S ribosomal subunit. Recently, numerous worldwide researches focused on their properties and possible involvement in cancer therapy have been conducted. Here, we evaluated in vitro the antiproliferative activity of some 5-(carbamoylmethylene)-oxazolidin-2-ones on MCF-7 and HeLa cells. Read More

View Article and Full-Text PDF
February 2020

[ C]Carbonyl Difluoride-a New and Highly Efficient [ C]Carbonyl Group Transfer Agent.

Angew Chem Int Ed Engl 2020 04 10;59(18):7256-7260. Epub 2020 Mar 10.

Molecular Imaging Branch, National Institute of Mental Health, National Institutes of Health, 10 Center Drive, Bethesda, MD, 20892-1003, USA.

Herein, the synthesis and use of [ C]carbonyl difluoride for labeling heterocycles with [ C]carbonyl groups in high molar activity is described. A very mild single-pass gas-phase conversion of [ C]carbon monoxide into [ C]carbonyl difluoride over silver(II) fluoride provides easy access to this new synthon in robust quantitative yield for labeling a broad range of cyclic substrates, for example, imidazolidin-2-ones, thiazolidin-2-ones, and oxazolidin-2-ones. Labeling reactions may utilize close-to-stoichiometric precursor quantities and short reaction times at room temperature in a wide range of solvents while also showing high water tolerability. Read More

View Article and Full-Text PDF

MnFeO magnetic nanoparticles modified with chitosan polymeric and phosphotungstic acid as a novel and highly effective green nanocatalyst for regio- and stereoselective synthesis of functionalized oxazolidin-2-ones.

Mater Sci Eng C Mater Biol Appl 2019 Dec 24;105:110109. Epub 2019 Aug 24.

Department of Chemistry, Faculty of Science, University of Kurdistan, Sanandaj, Iran. Electronic address:

A novel magnetically recoverable acid nanocatalyst, MnFeO/chitosan/phosphotungstic acid ([email protected]@PTA), was successfully synthesized. The synthesized nanoparticle was studied as the heterogenous nanocatalyst to prepare the functionalized oxazolidin-2-ones as versatile chiral synthons in asymmetrically synthesizing the compounds with biological activity through the reaction of α-epoxyketones with urea and thiourea. This new procedure has notable advantages such as excellent yields, green reaction conditions, and short reaction time. Read More

View Article and Full-Text PDF
December 2019

Stereocontrolled Synthesis of trans/ cis-2,3-Disubstituted Cyclopropane-1,1-diesters and Applications in the Syntheses of Furanolignans.

J Org Chem 2018 10 28;83(20):12549-12558. Epub 2018 Sep 28.

Key Laboratory of Functionalized Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecule-Based Materials (State Key Laboratory Cultivation Base), College of Chemistry and Materials Science , Anhui Normal University , Wuhu , Anhui 241000 , China.

A new Michael addition/intramolecular alkylation sequence of ( Z)-3-(2-bromo-3-arylacryloyl)oxazolidin-2-ones and malonates was developed. By a simple switch of the reaction conditions including the base promoter, solvent, and reaction temperature, both of the cis- and trans-isomers of a series of oxazolidinone-containing 2,3-disubstituted cyclopropane-1,1-diesters could be obtained in good-to-excellent yields and with an excellent diastereoselectivity. The utility of the cyclopropane products was demonstrated in the diastereoselective syntheses of (±)-urinaligran and a stereoisomer of (±)-virgatusin involving the AlCl-promoted [3+2] annulation with veraldehyde or piperonal as the key step. Read More

View Article and Full-Text PDF
October 2018

Stereoselective Synthesis of Highly Substituted Tetrahydropyrans through an Evans Aldol-Prins Strategy.

J Org Chem 2018 08 6;83(16):9039-9066. Epub 2018 Aug 6.

Instituto Universitario de Bio-Orgánica "Antonio González" (IUBO-AG), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Departamento de Química Orgánica , Universidad de La Laguna (ULL) , Avda. Astrofísico Francisco Sánchez 2 , 38206 San Cristóbal de La Laguna , Tenerife , Spain.

A direct and general method for the synthesis of naturally occurring 2,3,4,5,6-pentasubstituted tetrahydropyrans has been developed, employing β,γ-unsaturated N-acyl oxazolidin-2-ones as key starting materials. The combination of the Evans aldol addition and the Prins cyclization allowed the diastereoselective and efficient generation of the desired oxacycles in two fashions: a one-pot Evans aldol-Prins protocol, in which five new σ bonds and five contiguous stereocenters were straightforwardly generated, and a two-step version, which additionally permitted the isolation of β,γ-unsaturated alcohol precursors bearing an N-acyl oxazolidin-2-one in the α position. From these alcohols were also obtained halogenated pentasubstituted tetrahydropyrans as well as 2,3,4,5-tetrasubstituted tetrahydrofurans, shedding light on the mechanism of the process. Read More

View Article and Full-Text PDF

Optimization of 3-Pyrimidin-4-yl-oxazolidin-2-ones as Orally Bioavailable and Brain Penetrant Mutant IDH1 Inhibitors.

ACS Med Chem Lett 2018 Jul 11;9(7):746-751. Epub 2018 Jun 11.

Novartis Institutes for BioMedical Research, 250 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.

Mutant isocitrate dehydrogenase 1 (IDH1) is an attractive therapeutic target for the treatment of various cancers such as AML, glioma, and glioblastoma. We have evaluated 3-pyrimidin-4-yl-oxazolidin-2-ones as mutant IDH1 inhibitors that bind to an allosteric, induced pocket of IDH1. This Letter describes SAR exploration focused on improving both the and metabolic stability of the compounds, leading to the identification of as a potent and selective mutant IDH1 inhibitor that has demonstrated brain penetration and excellent oral bioavailability in rodents. Read More

View Article and Full-Text PDF

Synthesis, Spectroscopic Characterization, and Antibacterial Evaluation of Novel Functionalized Sulfamidocarbonyloxyphosphonates.

Molecules 2018 07 10;23(7). Epub 2018 Jul 10.

Laboratory of Applied Organic Chemistry, Synthesis of Biomolecules and Molecular Modelling Group, Badji-Mokhtar-Annaba University, Box 12, 23000 Annaba, Algeria.

Several new sulfamidocarbonyloxyphosphonates were prepared in two steps, namely carbamoylation and sulfamoylation, by using chlorosulfonyl isocyanate (CSI), α-hydroxyphosphonates, and various amino derivatives and related (primary or secondary amines, β-amino esters, and oxazolidin-2-ones). All structures were confirmed by ¹H, C, and P NMR spectroscopy, IR spectroscopy, and mass spectroscopy, as well as elemental analysis. Eight compounds were evaluated for their antibacterial activity against four reference bacteria including Gram-positive (ATCC 25923), and Gram-negative (ATCC 25922), (ATCC 700603), (ATCC 27853), in addition to three clinical strains of each studied bacterial species. Read More

View Article and Full-Text PDF

Glucosinolate turnover in Brassicales species to an oxazolidin-2-one, formed via the 2-thione and without formation of thioamide.

Phytochemistry 2018 Sep 7;153:79-93. Epub 2018 Jun 7.

Council for Agricultural Research and Economics, Research Centre for Cereal and Industrial Crops, Via di Corticella 133, 40128, Bologna, Italy.

Glucosinolates are found in plants of the order Brassicales and hydrolyzed to different breakdown products, particularly after tissue damage. In Barbarea vulgaris R.Br. Read More

View Article and Full-Text PDF
September 2018

Synthesis of Oxazolidin-2-ones from Unsaturated Amines with CO by Using Homogeneous Catalysis.

Chem Asian J 2018 Sep 24;13(17):2292-2306. Epub 2018 Jul 24.

Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, 29, Wangjiang Road, Chengdu, 610064, P. R. China.

Carbon dioxide (CO ), a well-known greenhouse gas, is also a nontoxic, readily accessible, and renewable one-carbon (C1) source. However, owing to its thermodynamic stability and kinetic inertness, the efficient utilization of CO is challenging. Much effort has been devoted to achieving efficient and selective organic transformations of CO . Read More

View Article and Full-Text PDF
September 2018

Asymmetric Diels-Alder Reaction of α,β-Unsaturated Oxazolidin-2-one Derivatives Catalyzed by a Chiral Fe(III)-Bipyridine Diol Complex.

Org Lett 2018 02 8;20(4):995-998. Epub 2018 Feb 8.

Département de Chimie, Université Laval , 1045 avenue de la Médecine, Québec, QC G1V 0A6, Canada.

An asymmetric Fe-bipyridine diol catalyzed Diels-Alder reaction of α,β-unsaturated oxazolidin-2-ones has been developed. Among various Fe/Fe salts, Fe(ClO)·6HO was selected as the Lewis acid of choice. The use of a low catalyst loading (2 mol % of Fe(ClO)·6HO and 2. Read More

View Article and Full-Text PDF
February 2018

Design, synthesis and biological activity of 3-pyrazine-2-yl-oxazolidin-2-ones as novel, potent and selective inhibitors of mutant isocitrate dehydrogenase 1.

Bioorg Med Chem 2017 12 13;25(24):6379-6387. Epub 2017 Oct 13.

Department of Pharmaceutical Engineering & Department of Biochemical Engineering, China Pharmaceutical University, 639 Longmian Avenue, Nanjing 211198, China; Department of Medicinal Chemistry, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, China. Electronic address:

Isocitrate dehydrogenases (IDHs) catalyze the oxidative decarboxylation of isocitrate to alpha-ketoglutarate (α-KG) generating carbon dioxide and NADPH/NADH. Evidence suggests that the specific mutations in IDH1 are critical to the growth and reproduction of some tumor cells such as gliomas and acute myeloid leukemia, emerging as an attractive antitumor target. In order to discovery potent new mutant IDH1 inhibitors, we designed, synthesized and evaluated a series of allosteric mIDH1 inhibitors harboring the scaffold of 3-pyrazine-2-yl-oxazolidin-2-ones. Read More

View Article and Full-Text PDF
December 2017

Discovery and Evaluation of Clinical Candidate IDH305, a Brain Penetrant Mutant IDH1 Inhibitor.

ACS Med Chem Lett 2017 Oct 18;8(10):1116-1121. Epub 2017 Sep 18.

Novartis Institutes for BioMedical Research, 250 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.

Inhibition of mutant IDH1 is being evaluated clinically as a promising treatment option for various cancers with hotspot mutation at Arg. Having identified an allosteric, induced pocket of IDH1, we have explored 3-pyrimidin-4-yl-oxazolidin-2-ones as mutant IDH1 inhibitors for modulation of 2-HG production and potential brain penetration. We report here optimization efforts toward the identification of clinical candidate (), a potent and selective mutant IDH1 inhibitor that has demonstrated brain exposure in rodents. Read More

View Article and Full-Text PDF
October 2017

Discovery of 3,5-Diphenyl-4-methyl-1,3-oxazolidin-2-ones as Novel, Potent, and Orally Available Δ-5 Desaturase (D5D) Inhibitors.

J Med Chem 2017 11 31;60(21):8963-8981. Epub 2017 Oct 31.

Pharmaceutical Research Division, Takeda Pharmaceutical Company Limited , 26-1, Muraoka-Higashi 2-chome, Fujisawa, Kanagawa 251-8555, Japan.

The discovery and optimization of Δ-5 desaturase (D5D) inhibitors are described. Investigation of the 1,3-oxazolidin-2-one scaffold was inspired by a pharmacophore model constructed from the common features of several hit compounds, resulting in the identification of 3,5-diphenyl-1,3-oxazolidin-2-one 5h as a novel lead showing potent in vitro activity. Subsequent optimization focused on the modification of two metabolic sites, which provided (4S,5S)-5i, a derivative with improved metabolic stability. Read More

View Article and Full-Text PDF
November 2017

PhI(OAc)-mediated 1,2-aminohalogenation of alkynes: a general access to (E)-4-(halomethylene)oxazolidin-2-ones.

Org Biomol Chem 2017 May;15(18):3964-3967

State Key Laboratory of Chemo/Biosensing and Chemometrics, Hunan University, Changsha 410082, China.

A new PhI(OAc)-mediated 1,2-aminohalogenation of prop-2-yn-1-yl carbamates and various halogen sources is presented with excellent selectivity and high step-economy. The reaction is general and rapid for the construction of diverse (E)-4-(halomethylene)oxazolidin-2-ones through the generation of the three-membered ring or N-radical followed by intramolecular cyclization. Read More

View Article and Full-Text PDF

Optimization of 3-Pyrimidin-4-yl-oxazolidin-2-ones as Allosteric and Mutant Specific Inhibitors of IDH1.

ACS Med Chem Lett 2017 Feb 16;8(2):151-156. Epub 2016 Dec 16.

Novartis Institutes for Biomedical Research , 250 Massachusetts Avenue, Cambridge, Massachusetts 02139, United States.

High throughput screening and subsequent hit validation identified 4-isopropyl-3-(2-((1-phenylethyl)amino)pyrimidin-4-yl)oxazolidin-2-one as a potent inhibitor of IDH1. Synthesis of the four separate stereoisomers identified the (,)-diastereomer (, ) as the most potent isomer. This also showed reasonable cellular activity and excellent selectivity vs IDH1. Read More

View Article and Full-Text PDF
February 2017

High-Valent Palladium-Promoted Formal Wagner-Meerwein Rearrangement.

Org Lett 2016 11 31;18(22):5804-5807. Epub 2016 Oct 31.

Institute of Chemistry and BioMedical Sciences, School of Chemistry and Chemical Engineering, Nanjing University , Nanjing 210093, P. R. China.

An oxy-palladation, formal Wagner-Meerwein rearrangement and fluorination cascade has been established for generating fluorinated oxazolidine-2,4-diones and oxazolidin-2-ones. The reaction has a broad substrate scope in which both aryl and alkyl groups can be utilized as efficient migrating groups. Experimental evidence suggests that the reaction is initiated by anti-oxy-palladation of the olefin, followed by oxidative generation of an alkyl Pd intermediate and a concerted migration-fluorination. Read More

View Article and Full-Text PDF
November 2016

Activation of aldehydes by exocyclic iridium(i)-η:π-diene complexes derived from 1,3-oxazolidin-2-ones.

Dalton Trans 2016 Nov 29;45(42):16878-16888. Epub 2016 Sep 29.

Área Académica de Química, Universidad Autónoma del Estado de Hidalgo, Carretera Pachuca-Tulancingo Km. 4.5, Mineral de la Reforma, Hidalgo 42090, México.

The Ir(i) complexes [TpIr(η-1,4-diene)] 2b and 2c react thermally with a variety of aromatic aldehydes, 3a-e, to generate the metallabicyclic compounds 4e-k and the Fischer-type carbenes 5a-b in moderate yields. These reactions are proposed to take place with the initial formation of η-aldehyde adducts as key intermediates. The formation of the metallabicyclic compounds 4e-k involves a formal decarboxylation process at the exo-2-oxazolidinone diene and an ortho metallation of the aromatic ring. Read More

View Article and Full-Text PDF
November 2016

Asymmetric Syntheses of (-)-ADMJ and (+)-ADANJ: 2-Deoxy-2-amino Analogues of (-)-1-Deoxymannojirimycin and (+)-1-Deoxyallonojirimycin.

J Org Chem 2016 08 15;81(15):6481-95. Epub 2016 Jul 15.

Department of Chemistry, Chemistry Research Laboratory, University of Oxford , Mansfield Road, Oxford OX1 3TA, United Kingdom.

The asymmetric syntheses of (-)-ADMJ and (+)-ADANJ, the 2-deoxy-2-amino analogues of (-)-1-deoxymannojirimycin and (+)-1-deoxyallonojirimycin, are described herein. Methodology for the ring-closing iodoamination of bishomoallylic amines followed by in situ ring-expansion (via intramolecular ring-opening of the corresponding aziridinium intermediates with a tethered carbamate moiety) to give oxazolidin-2-ones was initially optimized on a model system. Subsequent application of this methodology to two enantiopure bishomoallylic amines (which were produced via aminohydroxylation of an α,β-unsaturated ester, partial reduction, and reaction of the corresponding aldehyde with vinylmagnesium bromide) also proceeded with concomitant N-debenzylation to afford the corresponding diastereoisomerically pure (>99:1 dr) oxazolidin-2-ones. Read More

View Article and Full-Text PDF

(Enantio)selective Hydrogen Autotransfer: Ruthenium-Catalyzed Synthesis of Oxazolidin-2-ones from Urea and Diols.

Angew Chem Int Ed Engl 2016 06 13;55(27):7826-30. Epub 2016 Apr 13.

Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059, Rostock, Germany.

A novel strategy for the synthesis of oxazolidin-2-ones from vicinal diols and urea is described. In this heterocycle synthesis, two different C-O and C-N bonds are sequentially formed in a domino process consisting of nucleophilic substitution and alcohol amination. The use of readily available starting materials and the good atom economy render this process environmentally benign. Read More

View Article and Full-Text PDF

Synthesis of Oxazolidin-2-ones by Oxidative Coupling of Isonitriles, Phenyl Vinyl Selenone, and Water.

Chemistry 2016 Feb 8;22(7):2278-81. Epub 2016 Jan 8.

Laboratory of Synthesis and Natural Products, école Polytechnique Fédérale de Lausanne, EPFL-SB-ISIC-LSPN, BCH 5304, 1015, Lausanne, Switzerland.

Reaction of alkyl isocyanides, phenyl vinyl selenone, and water in the presence of a catalytic amount of Cs2 CO3 afforded oxazolidin-2-ones in good yields. This unprecedented heteroannulation process created four chemical bonds in a single operation with the isocyano group acting formally as a polarized double bond and phenyl vinyl selenone as a latent 1,3-dipole. The phenylselenonyl group played a triple role as an electron-withdrawing group to activate the 1,4-addition, a leaving group, and a latent oxidant in this transformation. Read More

View Article and Full-Text PDF
February 2016

Cinchona Alkaloid Catalyzed Sulfa-Michael Addition Reactions Leading to Enantiopure β-Functionalized Cysteines.

J Org Chem 2015 Nov 21;80(21):10561-74. Epub 2015 Oct 21.

Van't Hoff Institute for Molecular Sciences, Faculty of Science, The University of Amsterdam , Science Park 904, 1098 XH Amsterdam, The Netherlands.

Sulfa-Michael additions to α,β-unsaturated N-acylated oxazolidin-2-ones and related α,β-unsaturated α-amino acid derivatives have been enantioselectively catalyzed by Cinchona alkaloids functionalized with a hydrogen bond donating group at the C6' position. The series of Cinchona alkaloids includes known C6' (thio)urea and sulfonamide derivatives and several novel species with a benzimidazole, squaramide or a benzamide group at the C6' position. The sulfonamides were especially suited as bifunctional organocatalysts as they gave the products in very good diastereoselectivity and high enantioselectivity. Read More

View Article and Full-Text PDF
November 2015