Dedicated to Professor K. Peter C. Vollhardt with deep appreciation, where science
and art combine
Abstract
Oxidative palladium-catalyzed reaction conditions have been developed to allow for
regioselective and stereoselective coupling of allylic boronic esters with a range
of carbon-, oxygen-, and nitrogen-based nucleophiles. Studies into the mechanism of
the reaction have shown that the key transmetalation step occurs with retention of
stereochemistry, since overall inversion is observed.
Key words
palladium - boronic ester - umpolung - allylation - oxidative coupling