Synfacts 2008(8): 0829-0829  
DOI: 10.1055/s-2008-1077916
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Chiral Sulfamidates Preparation by Enantioselective Hydrogenation

Contributor(s): Mark Lautens, Frédéric Ménard
Y.-Q. Wang, C.-B. Yu, D.-W. Wang, X.-B. Wang, Y.-G. Zhou*
Dalian Institute of Chemical Physics and Shanghai Institute of Organic Chemistry, P. R. of China
Further Information

Publication History

Publication Date:
23 July 2008 (online)

Significance

Sulfamidates are generally prepared in many steps from the parent amino alcohols. An imine hydrogenation strategy makes access to chiral sulfamidates much simpler. The reaction was shown to tolerate a wide range of substituents. The cyclic imines subtrates are readily prepared by condensation the corresponding hydroxy ketones with ClSO2NH2. The free amines can be generated by reduction with LiAlH4.