Remote stereocenter discrimination in the enzymatic resolution of piperidine-2-ethanol. Short enantioselective synthesis of sedamine and allosedamine.
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.
Angoli
Marco
M
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.
Barilli
Alessio
A
Lesma
Giordano
G
Passarella
Daniele
D
Riva
Sergio
S
Silvani
Alessandra
A
Danieli
Bruno
B
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
D000470:Alkaloids; C482829:N-Boc-piperidine-2-ethanol; D010880:Piperidines; C459239:sedamine; C011350:sedridine; D008049:Lipase