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

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journal contribution
posted on 27.04.2007, 00:00 by Koushik Das Sarma, Ji Zhang, Timothy T. Curran
Novel 5-(1‘-hydroxy)-γ-butyrolactone and γ-butyrolactam subunits were synthesized by direct vinylogous aldol addition of α,β-dichloro γ-butyrolactones and γ-butyrolactams with aldehydes under basic conditions. Different bases and solvents were screened in the context of generating γ-butyrolactones. Diastereoselectivity was observed and γ-butenolides and γ-butyrolactams showed opposite diastereoselectivity under the same reaction condition.