Enantioselective Synthesis of Cyclic Sulfamidates

Significance

Cyclic sulfamidates are important precursors for the synthesis of 1,2-functionalized amine building blocks like 1,2-amino alcohols and α-amino acids. Herein, a rapid and mild procedure towards enantiomerically pure sulfamidates 2 starting from cyclic sulfamidate imines 1, using a rhodium-catalyzed asymmetric transfer hydrogenation is described. This protocol opens a route to these building blocks with very high yields and nearly perfect enantioselectivities. Moreover, the methodology was used in a short synthesis of the mexiletine analogue 7, which is an effective sodium channel blocker.