Remote stereocenter discrimination in the enzymatic resolution of piperidine-2-ethanol. Short enantioselective synthesis of sedamine and allosedamine |
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Authors: | Angoli Marco Barilli Alessio Lesma Giordano Passarella Daniele Riva Sergio Silvani Alessandra Danieli Bruno |
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Institution: | Dipartimento di Chimica Organica e Industriale e Centro Interdisciplinare Studi Biomolecolari e Applicazioni Industriali (CISI), Università degli Studi di Milano, Via Venezian 21, 20133 Milano, Italy. |
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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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