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Synfacts 2008(8): 0877-0877  
DOI: 10.1055/s-2008-1078544
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Imino Aza-enamine Reaction

Contributor(s): Benjamin List, Frank Lay
T. Hashimoto, M. Hirose, K. Maruoka*
Kyoto University, Japan
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Publication History

Publication Date:
23 July 2008 (online)

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Significance

The authors report the asymmetric addition of arylaldehyde N,N-dialkylhydrazones 1 to N-Boc imines 2 catalyzed by axially chiral dicarboxylic acid 3. α-Amino hydrazones 4 are obtained in moderate to good yields (35-77%), but very high enantiomeric ratios (er = 94.5:5.5 up to 97.5:2.5). Furthermore, the transformation into the corresponding α-amino ketones 5 by ozonolysis without loss of enantioselectivity is exemplified.