1993 Volume 22 Issue 8 Pages 1429-1432
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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