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Paper | Special issue | Vol 82, No. 2, 2010, pp.1411-1421
Published online, 14th January, 2011
DOI: 10.3987/COM-10-S(E)94
Enantioselective Synthesis of α-Methylene-γ-butyrolactams Using N-tert-Butanesulfinamides

Haythem K. Dema, Francisco Foubelo,* and Miguel Yus*

*Department of Organic Chemistry, Faculty of Sciences and Institute of Organic Synthesis (ISO), University of Alicante, P.O. Box 99, 03080 Alicante, Spain

Abstract

Indium-mediated coupling of ethyl 2-(bromomethyl)acrylate (1) and chiral N-tert-butanelsulfinylimines 2 in a saturated sodium bromide aqueous solution leads to N-tert-butanesulfinyl aminoesters 3 in high yields and diastereoselectivities. After column chromatography purification, enantiomerically pure aminoesters 3 were converted into the expected α-methylene-γ-butyrolactams 4 in a one-pot process.