Construction of perhydro indol-2-ones by a methoxide catalyzed deacetylation–Michael–aldol cascade

Abstract

An efficient, stereoselective Michael–aldol cascade for the one-pot construction of the perhydro indol-2-one bicyclic ring system using an acetate protected doubly-activated pyrrole-2-one pro-nucleophile and α,β-unsaturated carbonyl compounds has been developed. Initiated by a methoxide deacetylation in methanol at room temperature, the cascade is easy to perform, stereoselective, efficient and broad in scope to this synthetically relevant structure.