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DOI: 10.1055/s-0029-1219102
Asymmetric Synthesis of Cyclic Amino Alcohols via Dynamic Kinetic Resolution
S. Liu, J.-H. Xie, W. Li, W.-L. Kong, L.-X. Wang, Q.-L. Zhou*
Nankai University, Tianjin, P. R. of China
Publication History
Publication Date:
21 January 2010 (online)
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Significance
Asymmetric hydrogenation of racemic α-substituted ketones via dynamic kinetic resolution (DKR) is an efficient synthetic approach towards chiral alcohols with two adjacent stereo-centers. In the paper the authors report a successful application of this concept to a highly enantioselective synthesis of cis-β-N-alkyl/arylamino cyclic alcohols. The use of catalyst 1 allowed the preparation of a variety of products with high yields (>90%) and excellent enantio- and diastereoselectivities (cis/trans ratio from 97:3 to >99:1, 91-99% ee). This method provides access to enantiomerically enriched 2-(1-hydroxyalkyl)piperidines, an ubiquitous structural units in natural products. The described protocol was applied to the short and practical synthesis of all four isomers of the natural alkaloid conhydrine; the previously described synthetic protocols suffered from some tedious steps and low yields. The advantage of complex 1 seems to be apparent.