Catalyzed Tandem Reaction of 3-Silyloxy-1,5-enynes Consisting of Cyclization and Pinacol Rearrangement

摘要

The efficient construction of natural products and increasingly complex pharmaceutical agents requires the ongoing development of new methods for their stereocontrolled synthesis. Within this context, cationic cyclization reactions terminated by a pinacol rearrangement have been shown to be of exceptional value. For example, Overman and co-workers used a tandem reaction consisting of a Prins cyclization and a pinacol reaction for the synthesis of oxacyclic and carbocyclic natural products such as (-)-citreoviral and (+)-shahamin K. While various initiating groups have already been investigated in considerable detail, the activation of π systems in this context is not well understood.