title: Remote stereocenter discrimination in the enzymatic resolution of piperidine-2-ethanol. Short enantioselective synthesis of sedamine and allosedamine.
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.
authors: 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.
authors: Marco
authors: M
authors: Angoli
authors: Alessio
authors: A
authors: Barilli
authors: Giordano
authors: G
authors: Lesma
authors: Daniele
authors: D
authors: Passarella
authors: Sergio
authors: S
authors: Riva
authors: Alessandra
authors: A
authors: Silvani
authors: Bruno
authors: B
authors: Danieli
mesh_terms: D000107:Acetylation; D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D000818:Animals; D007700:Kinetics; D008049:Lipase / Q000737:chemistry / Q000378:metabolism; D008956:Models, Chemical; D015394:Molecular Structure; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; C482829:N-Boc-piperidine-2-ethanol; D010880:Piperidines; C459239:sedamine; C011350:sedridine; D008049:Lipase