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Synthesis 2008(18): 3009-3011  
DOI: 10.1055/s-2008-1067251
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© Georg Thieme Verlag Stuttgart ˙ New York

DBU-Catalyzed Addition Reactions of Sulfonylimidates

Ryosuke Matsubara, Shu Kobayashi*
Department of Chemistry, School of Science and Graduate School of Pharmaceutical Sciences, The University of Tokyo, The HFRE Division, ERATO, Japan Science Technology Agency (JST), Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
Fax: +81(3)56840634; e-Mail: shu_kobayashi@chem.s.u-tokyo.ac.jp;
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Publication History

Received 14 July 2008
Publication Date:
04 September 2008 (online)

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Abstract

Sulfonylimidates react with various types of N-protected imines in the presence of a catalytic amount of DBU to afford β-aminosulfonylimidates in high yields and high anti-selectivities. The experimental procedure is described in detail.

Key words

addition reaction - imine - catalysis - sulfonylimidate - direct reaction

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4

Thorough evaporation of the solvents provided the imidate HCl salt (a solid). The solidification of imidate salt could be encouraged by keeping it under argon at -20 ˚C. The exposure to air should be avoided as this salt readily absorbs moisture to form a gum-like solid, from which it was found to be difficult to remove the starting materials.