Enantio‐ and Regioconvergent Nickel‐Catalyzed C(sp 3 )−C(sp 3 ) Cross‐Coupling of Allylic Electrophiles Steered by a Silyl Group | Zendy

KranidiotisHisatomi Nektarios | Zendy; Yi Hong | Zendy; Oestreich Martin | Zendy

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Enantio‐ and Regioconvergent Nickel‐Catalyzed C(sp 3 )−C(sp 3 ) Cross‐Coupling of Allylic Electrophiles Steered by a Silyl Group

Author(s) -

KranidiotisHisatomi Nektarios,

Yi Hong,

Oestreich Martin

Publication year - 2021

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.202102233

Subject(s) - allylic rearrangement , electrophile , chemistry , stereocenter , vinylsilane , silylation , stereochemistry , medicinal chemistry , asymmetric induction , alkyl , catalysis , enantioselective synthesis , organic chemistry

A two‐step sequence for the enantio‐ and diastereoselective synthesis of exclusively alkyl‐substituted acyclic allylic systems with a stereocenter in the allylic position is reported. The asymmetric induction and the site selectivity are controlled in an enantio‐ and regioconvergent nickel‐catalyzed C(sp 3 )−C(sp 3 ) cross‐coupling of regioisomeric mixtures of racemic α‐/γ‐silylated allylic halides and primary alkylzinc reagents. The silyl group steers the allylic displacement towards the formation of the vinylsilane regioisomer, and the resulting C(sp 2 )−Si bond serves as a linchpin for the installation of various C(sp 3 ) substituents in a subsequent step.

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