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Synfacts 2008(9): 1006-1006
DOI: 10.1055/s-2008-1078650
DOI: 10.1055/s-2008-1078650
Polymer-Supported Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Palladium/Lipase-Catalyzed Asymmetric Reductive Acylation of Ketoximes
K. Han, J. Park*, M.-J. Kim*
Pohang University of Science and Technology, Korea
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. August 2008 (online)

Significance
The one-pot asymmetric synthesis of optically active amides 3a-h from ketoximes 1a-h with aluminum hydroxide supported palladium catalyst [Pd/AlO(OH)] and lipase (Novozym-435) is described. Thus, the reaction of ketoximes 1a-h (0.30 mmol) with 2 was carried out in the presence of Pd/AlO(OH), Novozym-435 (9 mg), and 4 A MS (100 mg) in toluene under H2 to give the corresponding amides 3a-h with high enantioselectivity (83-92% yield, 93-98% ee). Amide 3a (0.26 mmol, 98% ee) was reduced by LiAlH4 in THF to afford the secondary amine 4 in 97% yield with 98% ee.