Literature DB >> 18211073

Highly stereoselective oxy-michael additions to beta,gamma-unsaturated alpha-keto esters: rapid enantioselective synthesis of 3-hydroxybutenolides.

Xin Xiong1, Caroline Ovens, Adam W Pilling, John W Ward, Darren J Dixon.   

Abstract

The highly diastereoselective oxy-Michael addition of the "naked" anion of (6S)-methyl delta-lactol to gamma-substituted beta,gamma-unsaturated alpha-keto esters leading to the direct formation of THP*-protected gamma-hydroxy alpha-keto ester derivatives is described. Subsequent acid-mediated deprotection affords the 3-hydroxybutenolides in high yields.

Entities:  

Year:  2008        PMID： 18211073     DOI： 10.1021/ol702693m

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


  4 in total

1.  N-heterocyclic carbene-catalyzed conjugate additions of alcohols.

Authors:  Eric M Phillips; Matthias Riedrich; Karl A Scheidt
Journal:  J Am Chem Soc       Date:  2010-09-29       Impact factor: 15.419

2.  Stereoselective synthesis of 2-deoxy-beta-glycosides using anomeric O-alkylation/arylation.

Authors:  William J Morris; Matthew D Shair
Journal:  Org Lett       Date:  2009-01-01       Impact factor: 6.005

3.  Racemic hemiacetals as oxygen-centered pronucleophiles triggering cascade 1,4-addition/Michael reaction through dynamic kinetic resolution under iminium catalysis. Development and mechanistic insights.

Authors:  Ane Orue; Uxue Uria; David Roca-López; Ignacio Delso; Efraím Reyes; Luisa Carrillo; Pedro Merino; Jose L Vicario
Journal:  Chem Sci       Date:  2017-01-30       Impact factor: 9.825

4.  Insights into Ag(i)-catalyzed addition reactions of amino alcohols to electron-deficient olefins: competing mechanisms, role of catalyst, and origin of chemoselectivity.

Authors:  Chunhui Liu; Peilin Han; Zhizhong Xie; Zhihong Xu; Donghui Wei
Journal:  RSC Adv       Date:  2018-12-04       Impact factor: 4.036
  4 in total

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