Chemistry Letters
Online ISSN : 1348-0715
Print ISSN : 0366-7022
ISSN-L : 0366-7022
Stereoselective Synthesis of (Z)-(1-Organo-1-alkenyl)boronic Esters by the Palladium-Catalyzed Cross-Coupling Reaction of (Z)-(1-Iodo-1-alkenyl)boronic Esters with Organozinc Reagents
Tsukasa MoriyaNorio MiyauraAkira Suzuki
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1993 Volume 22 Issue 8 Pages 1429-1432

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Abstract

The cross-coupling reaction of organozinc reagents with a pinacol ester of (Z)-(1-iodo-1-hexenyl)boronic acid in the presence of Pd(PPh3)4 proceeded with complete retention of the configuration of the starting boronate. The reaction provided (E)-(1-organo-1-hexenyl)boronic esters which were not available by the conventional hydroboration technique. The utility of the reaction was demonstrated by stereoselective synthesis of an exocyclic alkene via the cross-coupling reaction with chloroenone.

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© 1993 The Chemical Society of Japan
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