A Solid-Supported Stereoselective Multicomponent Reaction: One-Pot Generation of Three Asymmetric Carbons

Herein, we describe a solid-supported stereoselective multicomponent reaction. One of the components, a (beta)-keto-(gamma)-lactam derived from alanine is generated in situ on the solid support and the addition of two equivalents of an aromatic aldehyde and one equivalent of urea generates a spiro-bicyclic (gamma)-lactam bearing three asymmetric carbons in a totally stereoselective manner resulting in a single product. The same reaction performed in solution displayed moderate stereoselectivity.