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Paper | Regular issue | Vol 71, No. 3, 2007, pp.531-542
Published online, 26th January, 2007
DOI: 10.3987/COM-06-10942
Diastereoselective Synthesis of Spiro-β-lactams via Staudinger Reaction

Susana Rojas-Lima,* Lidia Santillán-Sid, Heraclio López-Ruiz, and Alejandro Álvarez-Hernández

*Chemical Research Center (CIQ), Autonomous University of Hidalgo (UAEH) University City, Pachuca-Tulancingo road Km 4.5, Pachuca de Soto, Hidalgo, CP 42076, México

Abstract

In this work, eleven new spiro-β-lactams have been prepared using the Staudinger reaction of isomaleimides (1a-d) and carboxylic acids (chloroacetic acid, (-)-menthoxyacetic acid (7) and an oxazolidinone derived acid (10)) in the presence of triphosgene under mild condition. All reactions have been shown to be stereoselective. The new stereogenic centers were assigned by X-ray diffraction.