ABSTRACT

Allylation of carbonyl compounds (1) is arguably one of the most important and widely used carbon-carbon bond-forming reactions in organic synthesis (Scheme 14.1).1 The resulting homoallylic alcohols (2) are useful platforms for further synthetic elaboration, especially in the event that the allylation reaction proceeds stereoselectively.2 Accordingly, signicant effort over the past several decades has been aimed at the development of synthetic methodologies for effecting this carbon-carbon bond-forming reaction, including those that employ organometallic reagents like Grignard reagents, allylboranes, and allylsilanes.1 The latter, a Lewis acid-catalyzed reaction of a carbonyl with an allylsilane reagent, is known as the Hosomi-Sakurai or Sakurai reaction and has been extensively studied and applied in natural products synthesis.3