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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 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.201601636
Subject(s) - hydrosilylation , conjugate , enantioselective synthesis , rhodium , catalysis , chemistry , enantiomer , quaternary carbon , asymmetric induction , stereochemistry , medicinal chemistry , organic chemistry , mathematics , mathematical analysis
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.