Pubfacts - Scientific Publication Data
  • Categories
  • |
  • Journals
  • |
  • Authors
  • Login
  • Categories
  • Journals

Search Our Scientific Publications & Authors

Publications
  • Publications
  • Authors
find publications by category +
Translate page:

Brønsted Acid Catalyzed [6 + 2]-Cycloaddition of 2-Vinylindoles with in Situ Generated 2-Methide-2 H-pyrroles: Direct, Catalytic, and Enantioselective Synthesis of 2,3-Dihydro-1 H-pyrrolizines.

Authors:
Isa Kallweit Christoph Schneider

Org Lett 2019 01 8;21(2):519-523. Epub 2019 Jan 8.

Institut für Organische Chemie , Universität Leipzig , Johannisallee 29 , 04103 Leipzig , Germany.

We describe herein an organocatalytic, diastereo- and enantioselective [6 + 2]-cycloaddition toward the synthesis of densely substituted 2,3-dihydro-1 H-pyrrolizines bearing three contiguous stereogenic centers which are obtained with good yields, as single diastereomers, and with excellent enantioselectivity. A crucial feature of this one-step process leading to a prominent structural motif in many biologically active natural products is a BINOL-derived phosphoric acid catalyzed reaction of 1 H-pyrrole-2-yl carbinols with 2-vinylindoles via the corresponding hydrogen-bonded chiral 2-methide-2 H-pyrroles.

Download full-text PDF

Source
http://dx.doi.org/10.1021/acs.orglett.8b03833DOI Listing
January 2019

Publication Analysis

Top Keywords

acid catalyzed
8
2-methide-2 h-pyrroles
8
23-dihydro-1 h-pyrrolizines
8
enantioselectivity crucial
4
excellent enantioselectivity
4
feature one-step
4
process leading
4
one-step process
4
diastereomers excellent
4
crucial feature
4
yields single
4
bearing three
4
h-pyrrolizines bearing
4
substituted 23-dihydro-1
4
three contiguous
4
contiguous stereogenic
4
leading prominent
4
good yields
4
stereogenic centers
4
single diastereomers
4

Keyword Occurance

Similar Publications

Ruthenium-Catalyzed Intramolecular Double Hydrofunctionalization of Alkynes. Synthesis of Spirocyclic Hemiaminal Ethers and Their Lewis Acid-Mediated Cleavage/Nucleophilic Addition.

Authors:
Kazuma Nishimura Ryohei Hanzawa Tomoya Sugai Haruhiko Fuwa

J Org Chem 2021 Apr 16. Epub 2021 Apr 16.

Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.

[RuCl(-cymene)]/AgNO-catalyzed intramolecular double hydrofunctionalization of internal alkynes having nitrogen and oxygen nucleophilic groups at appropriate positions provided a series of spirocyclic hemiaminal ether derivatives in good to excellent yields. The product spiro-hemiaminal ethers underwent Lewis acid-mediated chemoselective cleavage, and in situ-generated iminium/oxocarbenium ions could be trapped with nucleophiles to afford a range of nitrogen and oxygen heterocycles. Read More

View Article and Full-Text PDF
April 2021
Similar Publications

Mediator-Enabled Electrocatalysis with Ligandless Copper for Anaerobic Chan-Lam Coupling Reactions.

Authors:
Benjamin R Walker Shuhei Manabe Andrew T Brusoe Christo S Sevov

J Am Chem Soc 2021 Apr 16. Epub 2021 Apr 16.

Department of Chemistry and Biochemistry, The Ohio State University, 151 W. Woodruff Avenue, Columbus, Ohio 43210, United States.

Simple copper salts serve as catalysts to effect C-X bond-forming reactions in some of the most utilized transformations in synthesis, including the oxidative coupling of aryl boronic acids and amines. However, these Chan-Lam coupling reactions have historically relied on chemical oxidants that limit their applicability beyond small-scale synthesis. Despite the success of replacing strong chemical oxidants with electrochemistry for a variety of metal-catalyzed processes, electrooxidative reactions with ligandless copper catalysts are plagued by slow electron-transfer kinetics, irreversible copper plating, and competitive substrate oxidation. Read More

View Article and Full-Text PDF
April 2021
Similar Publications

Hydrogen sulfide-An emerging signalling molecule regulating drought stress response in plants.

Authors:
Meenakshi Thakur Anjali Anand

Physiol Plant 2021 Apr 16. Epub 2021 Apr 16.

Division of Plant Physiology, ICAR-Indian Agricultural Research Institute, New Delhi, India.

Hydrogen sulfide (H S) is a small, reactive signalling molecule that is produced within chloroplasts of plant cells as an intermediate in the assimilatory sulfate reduction pathway by the enzyme sulfite reductase. Additionally, H S is also produced in cytosol and mitochondria by desulfhydration of L-cysteine catalyzed by L-cysteine desulfhydrase (DES1) in the cytosol and from β-cyanoalanine in mitochondria, in a reaction catalyzed by β-cyano-Ala synthase C1 (CAS-C1). H S exerts its numerous biological functions by post-translational modification involving oxidation of cysteine residues (RSH) to persulfides (RSSH). Read More

View Article and Full-Text PDF
April 2021
Similar Publications

Compensatory Transition of Bile Acid Metabolism from Fecal Disposition of Secondary Bile Acids to Urinary Excretion of Primary Bile Acids Underlies Rifampicin-Induced Cholestasis in Beagle Dogs.

Authors:
LanLan Gui QingLiang Wu YiTing Hu WuShuang Zeng XianWen Tan PingPing Zhu XueJing Li Lian Yang Wei Jia ChangXiao Liu Ke Lan

ACS Pharmacol Transl Sci 2021 Apr 22;4(2):1001-1013. Epub 2021 Mar 22.

Key Laboratory of Drug Targeting and Drug Delivery System, Ministry of Education, West China School of Pharmacy, Sichuan University, No. 17 People's South Road, Chengdu 610041, China.

Drug induced cholestasis (DIC) is complexly associated with dysbiosis of the host-gut microbial cometabolism of bile acids (BAs). Murine animals are not suitable for transitional studies because the murine BA metabolism is quite different from human metabolism. In this work, the rifampicin (RFP) induced cholestasis was established in beagle dogs that have a humanlike BA profile to disclose how RFP affects the host-gut microbial cometabolism of BAs. Read More

View Article and Full-Text PDF
April 2021
Similar Publications

Expression of Novel -Leucine Dehydrogenase and High-Level Production of -Tert-Leucine Catalyzed by Engineered .

Authors:
Yuan-Yuan Jia Yu-Li Xie Lu-Lu Yang Hong-Ling Shi Yun-Feng Lu Si-Pu Zhang Cun-Duo Tang Lun-Guang Yao Yun-Chao Kan

Front Bioeng Biotechnol 2021 30;9:655522. Epub 2021 Mar 30.

Henan Provincial Engineering Laboratory of Insect Bio-reactor, Henan Key Laboratory of Ecological Security for Water Source Region of Mid-line of South-to-North, Nanyang Normal University, Nanyang, China.

Leucine dehydrogenase (LDH) is a NAD-dependent oxidoreductase, which can selectively catalyze α-keto acids to obtain α-amino acids and their derivatives. It plays a key role in the biosynthesis of -tert-leucine (-Tle). As a non-naturally chiral amino acid, -Tle can be used as an animal feed additive, nutrition fortifier, which is a perspective and important building block in the pharmaceutical, cosmetic, and food additive industry. Read More

View Article and Full-Text PDF
March 2021
Similar Publications
© 2021 PubFacts.
  • About PubFacts
  • Privacy Policy
  • Sitemap