Remote stereocenter discrimination in the enzymatic resolution of piperidine-2-ethanol. Short enantioselective synthesis of sedamine and allosedamine.
J Org Chem
; 68(24): 9525-7, 2003 Nov 28.
Article
em En
| MEDLINE
| ID: mdl-14629188
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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Base de dados:
MEDLINE
Assunto principal:
Piperidinas
/
Alcaloides
Tipo de estudo:
Prognostic_studies
Limite:
Animals
Idioma:
En
Ano de publicação:
2003
Tipo de documento:
Article