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Diastereoselective Synthesis of Spiro-?-lactams via Staudinger Reactio



Lopez Ruiz, Heraclio

2007

Susana Rojas-Lima, Lidia Santillan-Sid, Heraclio López-Ruiz, and Alejandro Alvarez-Hernandez. Diastereoselective synthesis of spiro-beta-lactams via staudinger reaction. Heterocycles 71, 531-542 (2007). DOI: 10.3987/COM-06-10942.


Abstract


In this work, eleven new spiro-?-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.



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Diastereoselective Synthesis of Spiro-?-lactams via Staudinger Reactio