Literature DB >> 27436785

Catalytic Enantioselective Conjugate Additions of (pin)B-Substituted Allylcopper Compounds Generated in situ from Butadiene or Isoprene.

Xiben Li1, Fanke Meng1, Sebastian Torker1, Ying Shi1, Amir H Hoveyda2.   

Abstract

Multicomponent catalytic enantioselective transformations that entail the combination of butadiene or isoprene (common feedstock), an enoate (prepared in one step) and B2 (pin)2 (commercially available) are presented. These processes constitute an uncommon instance of conjugate addition of an allyl moiety and afford the desired products in up to 83 % yield and 98:2 enantiomeric ratio. Based on DFT calculations stereochemical models and rationale for the observed profiles in selectivity are provided.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  boron; conjugate additions; copper; enantioselective catalysis; synthetic methods

Mesh：

Substances：

Year:  2016        PMID： 27436785      PMCID： PMC5206808          DOI： 10.1002/anie.201605001

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN： 1433-7851            Impact factor:   15.336


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