Efficient synthesis of novel gamma-substituted gamma-butenolides by Lewis acid catalyzed addition of metal enolates of active methylene compounds to mucohalic acids

J Org Chem. 2005 Jul 22;70(15):5890-5. doi: 10.1021/jo050538t.

Abstract

Lewis acid catalyzed addition of active methylene compounds to mucochloric acid (1) and mucobromic acid (2) affording Knoevenagel aldol adducts, gamma-substituted gamma-butenolides, has been explored. Catalytic efficiencies of various Lewis acids have been compared. Indium acetate (0.25-5 mol %) was found to be the most efficient catalyst.