Construction of Quaternary Stereogenic Carbon Centers through Copper‐Catalyzed Enantioselective Allylic Cross‐Coupling with Alkylboranes | Zendy

Hojoh Kentaro | Zendy; Shido Yoshinori | Zendy; Ohmiya Hirohisa | Zendy; Sawamura Masaya | Zendy

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Construction of Quaternary Stereogenic Carbon Centers through Copper‐Catalyzed Enantioselective Allylic Cross‐Coupling with Alkylboranes

Author(s) -

Hojoh Kentaro,

Shido Yoshinori,

Ohmiya Hirohisa,

Sawamura Masaya

Publication year - 2014

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201402386

Subject(s) - stereocenter , allylic rearrangement , enantioselective synthesis , nucleophile , chemistry , allyl chloride , catalysis , coupling reaction , medicinal chemistry , reagent , stereochemistry , combinatorial chemistry , organic chemistry

A combination of an in situ generated chiral Cu I /DTBM‐MeO‐BIPHEP catalyst system and EtOK enabled the enantioselective S N 2′‐type allylic cross‐coupling between alkylborane reagents and γ,γ‐disubstituted primary allyl chlorides with enantiocontrol at a useful level. The reaction generates a stereogenic quaternary carbon center having three sp 3 ‐alkyl groups and a vinyl group. This protocol allowed the use of terminal alkenes as nucleophile precursors, thus representing a formal reductive allylic cross‐coupling of terminal alkenes. A reaction pathway involving addition/elimination of a neutral alkylcopper(I) species with the allyl chloride substrate is proposed.

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