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Synfacts 2006(4): 0391-0391  
DOI: 10.1055/s-2006-932104
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

Ketimine Reduction Employing a Pipecolic Acid Derived Organocatalyst

Contributor(s): Benjamin List, Sonja Mayer
Z. Wang, X. Ye, S. Wei, P. Wu, A. Zhang, J. Sun*
Chengdu Institute of Biology, Xihua University Chengdu and Wenzhou University, P. R. of China
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Publication History

Publication Date:
24 March 2006 (online)

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Significance

A wide range of N-aryl imines 2 could be reduced to the corresponding amines 3 with pipecolic acid derived catalyst 1. The reaction was carried out for 16 hours at 0 °C with a catalyst loading of 10 mol% and trichlorosilane as the hydride donor. The amines were formed in good to excellent yields (61-98%) and excellent enantioslectivities (85-96%). Increased enantioselectivities could be achieved by lowering the reaction temperature to -20 °C, whereas it was not possible to reduce the catalyst loading without significant loss of both, yield and enantioselectivity.