Remote Stereocenter Discrimination in the Enzymatic Resolution of Piperidine-2-ethanol. Short Enantioselective Synthesis of Sedamine and Allosedamine
The Journal of Organic Chemistry2003Vol. 68(24), pp. 9525–9527
Citations Over TimeTop 17% of 2003 papers
Marco Angoli, Alessio Barilli, Giordano Lesma, Daniele Passarella, Sergio Riva, Alessandra Silvani, Bruno Danieli
Abstract
Kinetic resolution of N-Boc-piperidine-2-ethanol (2), a case of remote stereocenter discrimination, was accomplished by sequential transesterification mediated by two enzymes, Lipase PS and porcine pancreatic lipase, showing opposite enantioselectivity. The gram-scale availability of the two enantiomeric N-Boc alcohols 2a (R) and 2c (S) enlarges their synthetic exploitation for the enantioselective preparation of piperidine alkaloids. As an example, the convenient three-step synthesis of both the enantiomers of sedamine and allosedamine is described.
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