Literature DB >> 16839156

One-pot asymmetric conjugate addition-trapping of zinc enolates by activated electrophiles.

Xavier Rathgeb1, Sébastien March, Alexandre Alexakis.   

Abstract

The copper-catalyzed asymmetric conjugate addition of dialkyl zinc leads to homochiral zinc enolates. These intermediates were trapped in situ with activated allylic electrophiles, without the need of additional palladium catalysis. High trans selectivity (85/15 to 100/0) and excellent enantioselectivities (up to 99%) could be attained. The functionalized nature of the electrophiles makes the new synthons potential candidates for further elaboration.

Entities:  

Year:  2006        PMID： 16839156     DOI： 10.1021/jo060814j

Source DB:  PubMed          Journal:  J Org Chem        ISSN： 0022-3263            Impact factor:   4.354


  4 in total

1.  (+)-Sorangicin A: evolution of a viable synthetic strategy.

Authors:  Amos B Smith; Shuzhi Dong; Richard J Fox; Jehrod B Brenneman; John A Vanecko; Tomohiro Maegawa
Journal:  Tetrahedron       Date:  2011-12-23       Impact factor: 2.457

2.  An efficient, second-generation synthesis of the signature dioxabicyclo[3.2.1]octane core of (+)-sorangicin A and elaboration of the (Z,Z,E)-triene acid system.

Authors:  Amos B Smith; Shuzhi Dong
Journal:  Org Lett       Date:  2009-03-05       Impact factor: 6.005

3.  Enantioselective total synthesis of (-)-nardoaristolone B via a gold(I)-catalyzed oxidative cyclization.

Authors:  Anna Homs; Michael E Muratore; Antonio M Echavarren
Journal:  Org Lett       Date:  2015-01-07       Impact factor: 6.005

4.  Role of TBATB in nano indium oxide catalyzed C-S bond formation.

Authors:  Prasanta Gogoi; Sukanya Hazarika; Pranjit Barman
Journal:  Sci Rep       Date:  2015-09-29       Impact factor: 4.379
  4 in total

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