Literature DB >> 12696870

Enantioselective synthesis of alpha-alkyl-beta,gamma-unsaturated esters through efficient cu-catalyzed allylic alkylations.

Kerry E Murphy1, Amir H Hoveyda.   

Abstract

A method for enantioselective Cu-catalyzed allylic substitution between various alkylzincs and alpha,beta-unsaturated carboxylic esters that bear a gamma-phosphate is reported. These transformations afford alpha-alkyl-beta,gamma-unsaturated carbonyls with regioselectivities of 7:1 to >20:1 (S(N)2':S(N)2) and in 87-97% ee. The utility of the method is illustrated by a convergent total synthesis of topoisomerse II inhibitor (R)-elenic acid.

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Year:  2003        PMID: 12696870     DOI: 10.1021/ja0300618

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN: 0002-7863            Impact factor:   15.419


  7 in total

1.  ROMP-derived oligomeric phosphates for application in facile benzylation.

Authors:  Toby R Long; Pradip K Maity; Thiwanka B Samarakoon; Paul R Hanson
Journal:  Org Lett       Date:  2010-07-02       Impact factor: 6.005

2.  Site- and enantioselective formation of allene-bearing tertiary or quaternary carbon stereogenic centers through NHC-Cu-catalyzed allylic substitution.

Authors:  Byunghyuck Jung; Amir H Hoveyda
Journal:  J Am Chem Soc       Date:  2012-01-03       Impact factor: 15.419

3.  Enantioselective Iridium-Catalyzed Allylic Alkylation Reactions of Masked Acyl Cyanide Equivalents.

Authors:  J Caleb Hethcox; Samantha E Shockley; Brian M Stoltz
Journal:  Org Lett       Date:  2017-03-14       Impact factor: 6.005

4.  Quaternary carbon stereogenic centers through copper-catalyzed enantioselective allylic substitutions with readily accessible aryl- or heteroaryllithium reagents and aluminum chlorides.

Authors:  Fang Gao; Yunmi Lee; Kyoko Mandai; Amir H Hoveyda
Journal:  Angew Chem Int Ed Engl       Date:  2010-11-02       Impact factor: 15.336

Review 5.  Catalytic enantioselective olefin metathesis in natural product synthesis. Chiral metal-based complexes that deliver high enantioselectivity and more.

Authors:  Amir H Hoveyda; Steven J Malcolmson; Simon J Meek; Adil R Zhugralin
Journal:  Angew Chem Int Ed Engl       Date:  2010       Impact factor: 15.336

6.  Synthesis of chiral mono(N-heterocyclic carbene) palladium and gold complexes with a 1,1'-biphenyl scaffold and their applications in catalysis.

Authors:  Lian-Jun Liu; Feijun Wang; Wenfeng Wang; Mei-Xin Zhao; Min Shi
Journal:  Beilstein J Org Chem       Date:  2011-05-04       Impact factor: 2.883

7.  Enantioselective α-functionalizations of ketones via allylic substitution of silyl enol ethers.

Authors:  Zhi-Tao He; John F Hartwig
Journal:  Nat Chem       Date:  2018-11-19       Impact factor: 24.427

  7 in total

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