z-logo
Premium
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
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201805476
Subject(s) - stereocenter , transmetalation , allylic rearrangement , zinc , chemistry , substitution (logic) , enantioselective synthesis , lithium (medication) , combinatorial chemistry , halide , substitution reaction , stereochemistry , medicinal chemistry , organic chemistry , catalysis , computer science , medicine , endocrinology , programming language
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.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here
Accelerating Research

Address

John Eccles House
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom