Journal of Organic Chemistry 2006-09-15

Stereoselective synthesis of highly functionalized nitrocyclopropanes via organocatalyic conjugate addition to nitroalkenes.

Séamus H McCooey, Thomas McCabe, Stephen J Connon

Index: J. Org. Chem. 71(19) , 7494-7, (2006)

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Abstract

A convenient and novel one-pot organocatalytic methodology for the stereoselective synthesis of highly functionalized nitrocyclopropanes is reported. The addition of dimethyl chloromalonate to a variety of nitroolefins catalyzed by tertiary amines leads to a Michael adduct which cyclizes to form the cyclopropane in the presence of DBU under carefully controlled reaction conditions with outstanding diastereoselectivity.