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Generation and Application of (Diborylmethyl)zinc(II) Species: Access to Enantioenriched gem ‐Diborylalkanes by an Asymmetric Allylic Substitution
Author(s) -
Lee Yeosan,
Park Jinyoung,
Cho Seung Hwan
Publication year - 2018
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.201805476
Subject(s) - stereocenter , transmetalation , allylic rearrangement , zinc , substitution (logic) , chemistry , enantioselective synthesis , lithium (medication) , combinatorial chemistry , medicinal chemistry , substitution reaction , stereochemistry , organic chemistry , catalysis , computer science , endocrinology , programming language , medicine
Abstract We report the successful generation of (diborylmethyl)zinc(II) species by transmetallation beteween isolable (diborylmethyl)lithium and zinc(II) halide (X=Br, Cl) and their application in the synthesis of enantioenriched gem ‐diborylalkanes bearing a stereogenic center at the β‐position of the diboryl groups by an asymmetric allylic substitution reaction. The reaction has a broad substrate scope, and various enantioenriched gem ‐diborylalkanes can be obtained in good yields with excellent enantioselectivity. Further elaboration of the enantioenriched gem ‐diborylalkanes provides access to a diverse set of valuable chiral building blocks.