The general and efficient palladium-catalyzed indium-mediated allylation of chiral hydrazones was accomplished with excellent yield (72-92%) and diastereoselectivity (up to 99:1). The development of this reaction as well as substrate scope is described. Conversion was found to be proportional to phosphine concentration, which provided insight into the mechanism and competing pathways of the redox transmetalation process.
“Highly Diastereoselective Palladium-Catalyzed Indium-Mediated Allylation of Chiral Hydrazones”
Narayanaganesh Balasubramanian, Tanmay Mandal, and Gregory R. Cook,*
Organic Letters 2015, 17, accepted for publication