Novel Synthons from Mucochloric Acid: The First Use of α,β-Dichloro-γ-butenolides and γ-Butyrolactams for Direct Vinylogous Aldol Addition

Abstract

Novel 5-(1'-hydroxy)-gamma-butyrolactone and gamma-butyrolactam subunits were synthesized by direct vinylogous aldol addition of alpha,beta-dichloro gamma-butyrolactones and gamma-butyrolactams with aldehydes under basic conditions. Different bases and solvents were screened in the context of generating gamma-butyrolactones. Diastereoselectivity was observed and gamma-butenolides and gamma-butyrolactams showed opposite diastereoselectivity under the same reaction condition.