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Stereodivergent Olefination of Enantioenriched Boronic Esters
Author(s) -
Armstrong Roly J.,
GarcíaRuiz Cristina,
Myers Eddie L.,
Aggarwal Varinder K.
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201610387
Subject(s) - chemistry , alkene , stereospecificity , stereoselectivity , electrophile , combinatorial chemistry , halogenation , halide , organic chemistry , catalysis
A stereodivergent coupling reaction between vinyl halides and boronic esters is described. This coupling process proceeds without a transition‐metal catalyst, instead proceeding by electrophilic selenation or iodination of a vinyl boronate complex followed by stereospecific syn or anti elimination. Chiral, nonracemic boronic esters could be coupled with complete enantiospecificity. The process enables the highly stereoselective synthesis of either the E or Z alkene from a single isomer of a vinyl coupling partner.