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Synfacts 2008(4): 0375-0375  
DOI: 10.1055/s-2008-1042795
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Stereoselective Catalytic Direct Additions of Sulfonylimidates

Contributor(s): Mark Lautens, Praew Thansandote
R. Matsubara, F. Berthiol, S. Kobayashi*
The University of Tokyo, Japan
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Publikationsdatum:
19. März 2008 (online)

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Significance

The authors describe the first examples of a highly stereoselective catalytic direct addition reaction of sulfonylimidates with Mannich-type, Michael-type, and azodicarboxylate acceptors. High anti-selectivity is observed for a large scope of substrates. The synthetic utility of the product is demonstrated through a variety of post-reaction modifications. An example of the direct formation of an α-amino acid derivative is also shown.