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Asymmetric Induction at Remote Quaternary Centers of Cyclohexadienones by Rhodium‐Catalyzed Conjugate Hydrosilylation
Author(s) -
Naganawa Yuki,
Kawagishi Mayu,
Ito Junichi,
Nishiyama Hisao
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201601636
Subject(s) - hydrosilylation , rhodium , conjugate , enantioselective synthesis , chemistry , asymmetric induction , catalysis , enantiomer , stereochemistry , combinatorial chemistry , organic chemistry , mathematical analysis , mathematics
The enantioselective desymmetrizing conjugate hydrosilylation of prochiral differently γ,γ‐disubstituted cyclohexadienone derivatives 2 to furnish the corresponding cyclohexenones 4 with a remote chiral all‐carbon quaternary center at the γ position is described. Chiral rhodium–bis(oxazolinyl)phenyl complexes 1 were effective catalysts for this transformation. This catalytic system was extended to the asymmetric transformation of spirocarbocyclic cyclohexadienones 5 to give the corresponding products 6 with high enantiomeric ratios.