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

Abstract

Herein, we describe a solid-supported stereoselective multicomponent reaction. One of the components, a β-keto-γ-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 γ-lactam bearing three asymmetric carbons in a totally stereoselective manner resulting in a single product. The same reaction performed in solution displayed moderate stereoselectivity.

Key words

multicomponent reaction - stereoselectivity - solid-phase organic synthesis - spiro-heterobicyclic system

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