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Paper | Regular issue | Vol 75, No. 10, 2008, pp.2429-2441
Published online, 23rd May, 2008
DOI: 10.3987/COM-08-11408
Aldolisation and Carboxylation Reactions from α-Silyl-β-lactams. A Combined Theoretical and Experimental Study

Sabrina Parat, Béatrice Pelotier, Lycia Fournier, Michel Rajzmann, Philip J. Kocienski, and Jean-Marc Pons*

*Institut des Sciences Moléculaires de Marseille (ISM2), Aix-Marseille Université, UMR-CNRS 6263, Campus de St-Jérôme, service 532, F-13397 Marseille Cedex 20, France

Abstract

Treatment of α-silyl-β-lactam 3 with TBAF in the presence of an aldehyde or carbon dioxide leads, with total trans stereoselectivity, to the corresponding aldol or carboxy adducts 5-6. Semiempirical calculations account for this result.