Journal of Organic Chemistry 2009-11-06

Rhodium-catalyzed synthesis of 3-hydroxy-beta-lactams via oxonium ylide generation: three-component reaction between azetidine-2,3-diones, ethyl diazoacetate, and alcohols.

Benito Alcaide, Pedro Almendros, Cristina Aragoncillo, Ricardo Callejo, M Pilar Ruiz, M Rosario Torres

Index: J. Org. Chem. 74(21) , 8421-4, (2009)

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Abstract

3-Substituted-3-hydroxy-beta-lactams, with two new adjacent stereogenic centers, have been prepared in a single step by a rhodium-catalyzed, three-component reaction between azetidine-2,3-diones, ethyl diazoacetate, and alcohols. Good to moderate stereoselectivity was obtained depending on the alcohol used. The stereochemistry of the new centers has been undoubtedly assigned by single crystal X-ray diffraction.