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

• DOI: 10.1021/jo062613l
• Publication Date: 2007-03-31T11:01:11Z
• Authors: Koushik Das Sarma; Ji Zhang; Timothy T. Curran
• Keywords: Aldol reaction; Synthon

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