Literature DB >> 16132090

A versatile catalyst for asymmetric reactions of carbonyl groups working purely by activation through hydrogen bonding: Mukaiyama-aldol, hetero Diels-Alder and Friedel-Crafts reactions.

Wei Zhuang1, Thomas B Poulsen, Karl Anker Jørgensen.   

Abstract

Bis-sulfonamides are demonstrated to be promising candidates for the efficient activation of carbonyl compounds through hydrogen bonding. Exemplified by three carbonyl addition reactions: Mukaiyama-aldol, hetero Diels-Alder and Friedel-Crafts reactions we show that bis-triflamides or bis-nonaflamides of commercially available chiral diamines act as chiral Brønsted-acid catalysts, leading to the optically active products in moderate to excellent yields and with enantioselectivities up to 73% ee.

Entities:  

Year:  2005        PMID: 16132090     DOI: 10.1039/b507778h

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  2 in total

1.  N-triflylthiophosphoramide catalyzed enantioselective Mukaiyama aldol reaction of aldehydes with silyl enol ethers of ketones.

Authors:  Cheol Hong Cheon; Hisashi Yamamoto
Journal:  Org Lett       Date:  2010-06-04       Impact factor: 6.005

2.  Novel bifunctional sulfonamides catalyze an enantioselective conjugate addition.

Authors:  Patrick G McGarraugh; Stacey E Brenner
Journal:  Tetrahedron       Date:  2009-01-10       Impact factor: 2.457

  2 in total

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