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Synfacts 2009(7): 0799-0799  
DOI: 10.1055/s-0029-1217301
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Switch in Direct Aminoxylation

Contributor(s): Benjamin List, Kristina Zumbansen
T. Kano, A. Yamamoto, F. Shirozu, K. Maruoka
Kyoto University, Japan
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Publication History

Publication Date:
22 June 2009 (online)

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Significance

A direct asymmetric aminoxylation of aldehydes and ketones is reported. Binaphthyl-based amino acid 1 and aminosulfonamide 2 were applied as catalysts in the reaction and a subsequent reduction afforded 2-aminoxy alcohols with good to excellent enantioselectivities. Remarkably, the binaphthyl-based chiral amine catalysts 1 and 2 which have the same axial chirality gave opposite enantiomers as the major product.