Asymmetric Induction at Remote Quaternary Centers of Cyclohexadienones by Rhodium‐Catalyzed Conjugate Hydrosilylation | Zendy

Naganawa Yuki | Zendy; Kawagishi Mayu | Zendy; Ito Junichi | Zendy; Nishiyama Hisao | Zendy

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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.

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