Literature DB >> 20161246

Catalytic enantioselective conjugate additions with α,β-unsaturated sulfones.

Hongming Li1, Jun Song, Li Deng.   

Abstract

We describe the development of a highly efficient catalytic asymmetric conjugate addition to α,β-unsaturated sulfones. Utilizing practical bifunctional organic catalysts and involving air- and moisture-tolerant conditions, conjugate additions of a wide range of Michael donors to α,β-unsaturated sulfones proceeded in excellent enantioselectivity/diastereoselectivity and high yield. This efficient and operationally simple new catalytic asymmetric reaction should provide a versatile approach for the asymmetric synthesis of chiral sulfones bearing all-carbon quaternary stereocenters.

Entities:  

Year:  2009        PMID: 20161246      PMCID: PMC2707842          DOI: 10.1016/j.tet.2008.11.054

Source DB:  PubMed          Journal:  Tetrahedron        ISSN: 0040-4020            Impact factor:   2.457


  23 in total

1.  Enantioselective Construction of Quaternary Stereocenters.

Authors:  Jens Christoffers; Alexander Mann
Journal:  Angew Chem Int Ed Engl       Date:  2001-12-17       Impact factor: 15.336

2.  Enantioselective nitroaldol reaction of alpha-ketoesters catalyzed by cinchona alkaloids.

Authors:  Hongming Li; Baomin Wang; Li Deng
Journal:  J Am Chem Soc       Date:  2006-01-25       Impact factor: 15.419

3.  Catalytic enantioselective C-C bond forming conjugate additions with vinyl sulfones.

Authors:  Hongming Li; Jun Song; Xiaofeng Liu; Li Deng
Journal:  J Am Chem Soc       Date:  2005-06-29       Impact factor: 15.419

Review 4.  Small-molecule H-bond donors in asymmetric catalysis.

Authors:  Abigail G Doyle; Eric N Jacobsen
Journal:  Chem Rev       Date:  2007-12       Impact factor: 60.622

5.  Catalytic enantioselective addition of diorganozinc reagents to vinyl sulfones.

Authors:  Jean-Nicolas Desrosiers; William S Bechara; André B Charette
Journal:  Org Lett       Date:  2008-05-08       Impact factor: 6.005

6.  Enantioselective Friedel-Crafts reaction of indoles with carbonyl compounds catalyzed by bifunctional cinchona alkaloids.

Authors:  Hongming Li; Yong-Qiang Wang; Li Deng
Journal:  Org Lett       Date:  2006-08-31       Impact factor: 6.005

7.  First enantioselective organocatalytic conjugate addition of aldehydes to vinyl phosphonates.

Authors:  Sarah Sulzer-Mossé; Matthieu Tissot; Alexandre Alexakis
Journal:  Org Lett       Date:  2007-08-23       Impact factor: 6.005

8.  Rhodium-catalyzed enantioselective conjugate addition of organoboronic acids to alpha,beta-unsaturated sulfones.

Authors:  Pablo Mauleón; Juan C Carretero
Journal:  Org Lett       Date:  2004-09-02       Impact factor: 6.005

9.  Catalytic asymmetric conjugate addition of grignard reagents to alpha,beta-unsaturated sulfones.

Authors:  Pieter H Bos; Adriaan J Minnaard; Ben L Feringa
Journal:  Org Lett       Date:  2008-09-04       Impact factor: 6.005

10.  Catalytic enantioselective reduction of beta,beta-disubstituted vinyl phenyl sulfones by using bisphosphine monoxide ligands.

Authors:  Jean-Nicolas Desrosiers; André B Charette
Journal:  Angew Chem Int Ed Engl       Date:  2007       Impact factor: 15.336

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  2 in total

Review 1.  Chalcone: A Privileged Structure in Medicinal Chemistry.

Authors:  Chunlin Zhuang; Wen Zhang; Chunquan Sheng; Wannian Zhang; Chengguo Xing; Zhenyuan Miao
Journal:  Chem Rev       Date:  2017-05-10       Impact factor: 60.622

2.  Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions.

Authors:  Alejandro Cabanillas; Christopher D Davies; Louise Male; Nigel S Simpkins
Journal:  Chem Sci       Date:  2014-11-28       Impact factor: 9.825

  2 in total

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