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Synfacts 2008(1): 0063-0063  
DOI: 10.1055/s-2007-991485
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Amination of Silyl Enol Ethers

Contributor(s): Mark Lautens, Frédéric Ménard
M. Anada, M. Tanaka, T. Washio, M. Yamawaki, T. Abe, S. Hashimoto*
Hokkaido University, Sapporo, Japan
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Publication History

Publication Date:
18 December 2007 (online)

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Significance

Chiral α-aminoketones are most often used in their reduced form as syn- or antiα-amino alcohols. A number of procedures have been developed to access such amino alcohols (or their precursors), but the above method complements the previous ones and provides an experimentally simple protocol. The one-pot sequence (7 to 4a) circumventing the potentially sensitive handling of silyl enol ethers 1 is particularly attractive. The Rh(II) catalyst 3 catalyzes both reactions efficiently by sequential addition of a hydride, then the iodoimine.