Literature DB >> 17956114

An enantioselective route to alpha-methyl carboxylic acids via metal and enzyme catalysis.

Jakob Norinder1, Krisztián Bogár, Lisa Kanupp, Jan-E Bäckvall.   

Abstract

Dynamic kinetic resolution of allylic alcohols to allylic acetates followed by copper-catalyzed allylic substitution gave alkenes in high yields and high optical purity. Subsequent oxidative C-C double bond cleavage afforded pharmaceutically important alpha-methyl substituted carboxylic acids in high ee.

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Year:  2007        PMID： 17956114     DOI： 10.1021/ol702261t

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  6 in total

Review 1.  Enantioselective and Enantiospecific Transition-Metal-Catalyzed Cross-Coupling Reactions of Organometallic Reagents To Construct C-C Bonds.

Authors:  Alan H Cherney; Nathaniel T Kadunce; Sarah E Reisman
Journal:  Chem Rev       Date:  2015-08-13       Impact factor: 60.622

2.  In Pursuit of an Ideal C-C Bond-Forming Reaction: Development and Applications of the Hydrovinylation of Olefins.

Authors:  T V Rajanbabu
Journal:  Synlett       Date:  2009       Impact factor: 2.454

3.  Use of a robust dehydrogenase from an archael hyperthermophile in asymmetric catalysis-dynamic reductive kinetic resolution entry into (S)-profens.

Authors:  Jacob A Friest; Yukari Maezato; Sylvain Broussy; Paul Blum; David B Berkowitz
Journal:  J Am Chem Soc       Date:  2010-05-05       Impact factor: 15.419

4.  Catalytic asymmetric synthesis using feedstocks: an enantioselective route to 2-arylpropionic acids and 1-arylethyl amines via hydrovinylation of vinyl arenes.

Authors:  Craig R Smith; T V RajanBabu
Journal:  J Org Chem       Date:  2009-04-17       Impact factor: 4.354

Review 5.  Chemoenzymatic dynamic kinetic resolution: a powerful tool for the preparation of enantiomerically pure alcohols and amines.

Authors:  Oscar Verho; Jan-E Bäckvall
Journal:  J Am Chem Soc       Date:  2015-03-19       Impact factor: 15.419

6.  Enantiospecific, nickel-catalyzed cross-couplings of allylic pivalates and arylboroxines.

Authors:  Harathi D Srinivas; Qi Zhou; Mary P Watson
Journal:  Org Lett       Date:  2014-06-13       Impact factor: 6.005
  6 in total

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