Synfacts 2010(11): 1274-1274  
DOI: 10.1055/s-0030-1258793
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Synthesis of Cyclic Sulfamidates

Contributor(s): Mark Lautens, Norman Nicolaus
S. Kang, J. Han, E. S. Lee, E. B. Choi, H.-K. Lee*
Korea Research Institute of Chemical Technology and University of Science and Technology, Daejeon, Korea
Further Information

Publication History

Publication Date:
21 October 2010 (online)

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.