Asymmetric synthesis of proline-based conformationally constrained tryptophan mimetic

Abstract

The synthesis of an optically pure proline-based tryptophan mimetic is described. The strategy involves the in situ generation of an unprecedented allylmetal species containing the indole moiety, and its coupling with a chiral imine. The construction of the 3-substitued proline skeleton is then achieved through a hydrozirconation/iodination sequence applied to the resulting homoallylic amine.