Stereodivergent Olefination of Enantioenriched Boronic Esters | Zendy

Armstrong Roly J. | Zendy; GarcíaRuiz Cristina | Zendy; Myers Eddie L. | Zendy; Aggarwal Varinder K. | Zendy

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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 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.201610387

Subject(s) - alkene , stereospecificity , chemistry , stereoselectivity , electrophile , combinatorial chemistry , halogenation , halide , catalysis , organic chemistry

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.

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