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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
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Publikationsdatum:
23. Juli 2008 (online)

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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.