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Catalytic Enantioselective Conjugate Additions of (pin)B‐Substituted Allylcopper Compounds Generated in situ from Butadiene or Isoprene
Author(s) -
Li Xiben,
Meng Fanke,
Torker Sebastian,
Shi Ying,
Hoveyda Amir H.
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201605001
Subject(s) - conjugate , enantioselective synthesis , isoprene , catalysis , in situ , 1,3 butadiene , chemistry , organic chemistry , combinatorial chemistry , stereochemistry , copolymer , polymer , mathematics , mathematical analysis
Multicomponent catalytic enantioselective transformations that entail the combination of butadiene or isoprene (common feedstock), an enoate (prepared in one step) and B 2 (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.