Organic Letters 2011-04-01

Synthesis and functionalization of 3-alkylidene-1,2-diazetidines using transition metal catalysis.

Michael J Brown, Guy J Clarkson, Graham G Inglis, Michael Shipman

Index: Org. Lett. 13(7) , 1686-9, (2011)

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Abstract

An efficient two-step synthesis of a wide range of 3-methylene-1,2-diazetidines has been developed through application of a Cu(I)-catalyzed 4-exo ring closure. The double bond of this new class of strained heterocycle can be functionalized in a stereocontrolled manner by using palladium-catalyzed Heck reactions. Moreover, chemoselective reduction of 3-alkylidene-1,2-diazetidines gives access to saturated 1,2-diazetidines and vicinal diamines.