Publications by authors named "Bao-Dong Cui"

12 Publications

  • Page 1 of 1

Palladium-catalyzed asymmetric allylic alkylation of 3-aminooxindoles to access chiral homoallylic aminooxindoles.

Org Biomol Chem 2021 Jun;19(21):4720-4725

Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi 563000, China. and Key Laboratory of Basic Pharmacology of Ministry of Education and Joint International Research Laboratory of Ethnomedicine of Ministry of Education, Zunyi Medical University, Zunyi 563000, China.

An organometal catalytic conversion of 3-aminooxindoles for the diastereo- and enantioselective synthesis of homoallylic aminooxindoles has been described. The asymmetric allylic alkylation of 3-aminooxindoles with allyl carboxylates proceeded smoothly to afford a series of chiral 3-allyl-3-aminooxindoles. This work offers an alternative route to build these scaffolds. The application of this protocol is also highlighted by a significant conversion of products to the potential applicable spiro[indoline-3,2'-pyrrolidin]-2-one derivatives.
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http://dx.doi.org/10.1039/d1ob00550bDOI Listing
June 2021

Synthesis of chromone-containing polycyclic compounds via palladium-catalyzed [2 + 2 + 1] annulation.

Org Biomol Chem 2020 02 27;18(6):1112-1116. Epub 2020 Jan 27.

Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, Green Pharmaceuticals Engineering Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi 563006, P. R. China. and Key Laboratory of Basic Pharmacology of Ministry of Education and Joint International Research Laboratory of Ethnomedicine of Ministry of Education, Zunyi Medical University, Zunyi 563006, P. R. China.

A palladium-catalyzed [2 + 2 + 1] domino annulation of 3-iodochromones, α-bromo carbonyl compounds, and tetracyclododecene (TCD) is described. This approach provides a facile, efficient and atom-economical route to a variety of chromone-containing polycyclic compounds bearing fused/bridged-ring systems in good yields (up to 81%) with excellent diastereoselectivities (99 : 1 dr in all cases).
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http://dx.doi.org/10.1039/c9ob02690hDOI Listing
February 2020

Generation of Difluorodiazoethane (CFHCHN): Application in the Regioselective Synthesis of CFH-Containing Pyrazoles.

Org Lett 2019 11 23;21(21):8751-8755. Epub 2019 Oct 23.

Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, School of Pharmacy , Zunyi Medical University , Zunyi 563006 , P. R. China.

A new method for the generation of difluorodiazoethane (CFHCHN) and a procedure for its efficient use in [3 + 2] cycloaddition with nitroolefins by the AcOH/O catalyst system were developed by using a simple two-chamber system. The method provides a facile and straightforward access to a series of 4-substituted 5-difluoromethyl-3-nitro-1-pyrazoles that are of interest in medicinal chemistry. Interestingly, the key factor for the success of this method is the efficient preparation of CFHCHN by an process.
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http://dx.doi.org/10.1021/acs.orglett.9b03371DOI Listing
November 2019

2,2-Bifunctionalization of Norbornene in Palladium-Catalyzed Domino Annulation.

Org Lett 2019 11 22;21(21):8857-8860. Epub 2019 Oct 22.

Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, Generic Drug Research Center of Guizhou Province, School of Pharmacy , Zunyi Medical University , Zunyi 563006 , PR China.

A palladium-catalyzed three-component [2 + 3 + 1] domino annulation among 3-iodochromones, α-bromoacetophenones, and norbornene is presented, affording various chromone-containing polycyclic compounds bearing fused/spiro/bridged-ring systems. For the first time, the 2,2-bifunctionalization of norbornene was realized in palladium-catalyzed domino reaction. This cyclization characterizes three new bonds (two C-C and one C-O) in a single operation and produces nontrivial spiro-norbornane fragments in comparison with a traditional palladium-catalyzed process involving norbornene.
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http://dx.doi.org/10.1021/acs.orglett.9b03565DOI Listing
November 2019

Asymmetric [3 + 2] Cycloaddition Reaction of Isatin-Derived MBH Carbonates with 3-Methyleneoxindoles: Enantioselective Synthesis of 3,3'-Cyclopentenyldispirooxindoles Incorporating Two Adjacent Quaternary Spirostereocenters.

J Org Chem 2018 09 11;83(17):10465-10475. Epub 2018 Jul 11.

Generic Drug Research Center of Guizhou Province, School of Pharmacy , Zunyi Medial University , Zunyi 563000 , China.

A highly regio- and stereoselective [3 + 2] cycloaddition reaction for constructing novel 3,3'-cyclopentenyldispirooxindoles incorporating two adjacent quaternary spirostereocenters is reported. Under the mild conditions, the asymmetric annulation of isatin-derived MBH carbonates with 3-methyleneoxindoles involving a chiral tertiary amine catalyst provides the corresponding dispirooxindole frameworks with an extraordinary level of enantioselective control. Further synthetic utility of this method was demonstrated by the gram-scale experiment and simple transformation of the obtained product. Moreover, a plausible mechanism for this annulation reaction was also proposed on the basis of the control experiments.
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http://dx.doi.org/10.1021/acs.joc.8b01506DOI Listing
September 2018

A Protocol for the Synthesis of CFH-Containing Pyrazolo[1,5- c]quinazolines from 3-Ylideneoxindoles and in Situ Generated CFHCHN.

J Org Chem 2018 06 4;83(12):6556-6565. Epub 2018 Jun 4.

Generic Drug Research Center of Guizhou Province, Green Pharmaceuticals Engineering Research Center of Guizhou Province, School of Pharmacy , Zunyi Medical University , Zunyi 563000 , China.

Herein is disclosed a selective and facile approach for the construction of CFH-containing pyrazolo[1,5- c]quinazolines from easily accessible 3-ylideneoxindoles and in situ generated CFHCHN. The reaction involving a [3 + 2] cycloaddition/1,3-H shift/rearrangement/dehydrogenation cascade proceeded smoothly at room temperature in the absence of catalyst and additive. Moreover, this metal-free process along with mild conditions is desirable and valuable for the pharmaceutical industry. Importantly, this reaction features a broad substrate scope, good functional group tolerance, and gram-scale synthesis.
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http://dx.doi.org/10.1021/acs.joc.8b00866DOI Listing
June 2018

Diastereoselective [3 + 2] cycloaddition of 3-ylideneoxindoles with in situ generated CFHCHN: syntheses of CFH-containing spirooxindoles.

Org Biomol Chem 2017 Jul;15(26):5571-5578

Generic Drug Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, 563000, China.

An efficient [3 + 2] cycloaddition of 3-ylideneoxindoles with in situ generated CFHCHN for the syntheses of spirooxindoles has been developed. This methodology gives access to a range of relatively complex spirooxindoles featuring a CFH group and three contiguous stereogenic centers in up to 84% yield and 99 : 1 trans/cis.
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http://dx.doi.org/10.1039/c7ob01266gDOI Listing
July 2017

RNA-seq transcriptome analysis of a Pseudomonas strain with diversified catalytic properties growth under different culture medium.

Microbiologyopen 2016 08 6;5(4):626-36. Epub 2016 Apr 6.

School of Pharmacy, Zunyi Medical University, Zunyi, 563000, China.

Biocatalysis is an emerging strategy for the production of enantio-pure organic molecules. However, lacking of commercially available enzymes restricts the widespread application of biocatalysis. In this study, we report a Pseudomonas strain which exhibited versatile oxidation activity to synthesize chiral sulfoxides when growing under M9-toluene medium and reduction activity to synthesize chiral alcohols when on Luria-Bertani (LB) medium, respectively. Further comparative transcriptome analysis on samples from these two cultural conditions has identified 1038 differentially expressed genes (DEG). Gene Ontology (GO) enrichment and KEGG pathways analysis demonstrate significant changes in protein synthesis, energy metabolism, and biosynthesis of metabolites when cells cultured under different conditions. We have identified eight candidate enzymes from this bacterial which may have the potential to be used for synthesis of chiral alcohol and sulfoxide chemicals. This work provides insights into the mechanism of diversity in catalytic properties of this Pseudomonas strain growth with different cultural conditions, as well as candidate enzymes for further biocatalysis of enantiomerically pure molecules and pharmaceuticals.
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http://dx.doi.org/10.1002/mbo3.357DOI Listing
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4985596PMC
August 2016

Organocatalytic Asymmetric Michael/Friedel-Crafts Cascade Reaction of 3-Pyrrolyl-oxindoles and α,β-Unsaturated Aldehydes for the Construction of Chiral Spiro[5,6-dihydropyrido[1,2-a]pyrrole-3,3'-oxindoles].

J Org Chem 2015 Jun 26;80(11):5951-7. Epub 2015 May 26.

†National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.

An efficient and unprecedented organocatalytic asymmetric reaction of 3-pyrrolyl-oxindoles with α,β-unsaturated aldehydes to generate spirocyclic oxindole compounds was developed. The reactions were catalyzed by diphenylprolinol silyl ether and 2-fluorobenzoic acid via an asymmetric Michael/Friedel-Crafts cascade process, followed by dehydration with p-toluenesulfonic acid to afford a wide variety of structurally diverse spiro[5,6-dihydropyrido[1,2-a]pyrrole-3,3'-oxindole] derivatives in high yields (up to 93%) and with high to excellent diastereo- and enantioselectivities (up to >99:1 dr and 97% ee).
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http://dx.doi.org/10.1021/acs.joc.5b00597DOI Listing
June 2015

3-Pyrrolyl-oxindoles as efficient nucleophiles for organocatalytic asymmetric synthesis of structurally diverse 3,3'-disubstituted oxindole derivatives.

Chem Commun (Camb) 2015 Jan 25;51(4):757-60. Epub 2014 Nov 25.

National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.

A range of 3-pyrrolyl-3,3'-disubstituted oxindoles were smoothly obtained via the reaction of 3-pyrrolyl-oxindoles with nitroalkenes using an organocatalyst. The usefulness of the protocol was also demonstrated by the versatile conversions of the Michael adducts into other functionalized 3,3'-disubstituted oxindoles, as well as into the analogues of some valuable natural products.
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http://dx.doi.org/10.1039/c4cc08364dDOI Listing
January 2015

Tandem Michael addition-ring transformation reactions of 3-hydroxyoxindoles/3-aminooxindoles with olefinic azlactones: direct access to structurally diverse spirocyclic oxindoles.

J Org Chem 2014 Jun 9;79(11):5305-14. Epub 2014 May 9.

National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences , Chengdu 610041, China.

An efficient method for the direct construction of two classes of spirocyclic oxindoles by the reactions of 3-hydroxyoxindoles/3-aminooxindoles and (Z)-olefinic azlactones through a tandem Michael addition-ring transformation process has been developed. With DBU as the catalyst, a range of spiro-butyrolactoneoxindoles and spiro-butyrolactamoxindoles, containing an oxygen or a nitrogen heteroatom, respectively, in the spiro stereocenter, were smoothly obtained with good to excellent diastereoselectivities in high yields.
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http://dx.doi.org/10.1021/jo500432cDOI Listing
June 2014

Enantioselective synthesis of quaternary 3-aminooxindoles via organocatalytic asymmetric Michael addition of 3-monosubstituted 3-aminooxindoles to nitroolefins.

J Org Chem 2013 Sep 21;78(17):8833-9. Epub 2013 Aug 21.

National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China.

An enantioselective synthesis of quaternary 3-aminooxindoles with 3-monosubstituted 3-aminooxindoles as nucleophiles is first presented. A Michael addition reaction of 3-monosubstituted 3-aminooxindoles to nitroolefins has been developed with a bifunctional thiourea-tertiary amine as a catalyst to afford a range of 3,3-disubstituted oxindoles bearing adjacent quaternary-tertiary centers in good results (up to 98% yield, >99:1 dr, and 92% ee). We also demonstrate the potential synthetic utility of this methodology by a transformation of the product into a spirocyclic oxindole compound.
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http://dx.doi.org/10.1021/jo401154bDOI Listing
September 2013
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