Stereoselective Synthesis of Functionalized Pyrrolidines via a [3 + 2]-Annulation of N-Ts-alpha-Amino Aldehydes and 1,3-Bis(silyl)propenes

摘要

The stereoselective synthesis of functionalized pyrrolidines is a topic of considerable interest,due to their great abundance in natural products and wide applications as chiral ligands and organocata-lysts in asymmetric synthesis.Consequently,significant efforts have been devoted to the development of efficient routes to substituted pyrrolidines.Recent examples include 1,3-dipolar cy-cloadditions of azomethine ylides to electron-deficient alkenes,reduction of pyrroles,intramolecular hydroaminations,and an-nulation reactions of allyl-,vinyl-,and allenesilanes.However,the efficient construction of polysubstituted pyrrolidines with well-defined stereochemistry and derivatizable functional groups remains a challenge in organic synthesis.The Lewis acid promoted addition of allylsilanes to- aldehydes is an important method for stereoselective C-C bond formation.