skip to main content

First stereocontrolled acetylation of a hydroxypropargylpiperidone by lipase CALB

Melgar, Gliseida Z. ; Wendler, Edison P. ; Dos Santos, Alcindo A. ; Porto, André L.M.

Tetrahedron: Asymmetry, 2010, Vol.21(18), pp.2271-2274 [Periódico revisado por pares]

Texto completo disponível

Ver todas as versões
Citações Citado por
  • Título:
    First stereocontrolled acetylation of a hydroxypropargylpiperidone by lipase CALB
  • Autor: Melgar, Gliseida Z. ; Wendler, Edison P. ; Dos Santos, Alcindo A. ; Porto, André L.M.
  • Assuntos: Chemistry
  • É parte de: Tetrahedron: Asymmetry, 2010, Vol.21(18), pp.2271-2274
  • Descrição: Hydroxypropargylpiperidones rac- 1– 3 were efficiently obtained by a one-pot three-component coupling reaction; enantioenriched propargylpiperidones were then obtained by a kinetic resolution process using the lipase from Candida antarctica. Lipase CALB has been shown to efficiently catalyse the stereocontrolled acetylation of hydroxypropargylpiperidones rac- 3 by promoting stereodiscrimination at the carbinolic centre. The enzymatic catalytic processes allow the separation of the ( S, R)- and ( S, S)- 3 diastereoisomers into the corresponding acetates produced as a ( R, S)- and ( R, R)- 6 diastereoisomeric pair. The CALB was able to discriminate the stereogenic centre of the secondary ( R) -enantiomer of rac- 3 according to the Kaslauzkas rule. The remote stereogenic centre was not discriminated by the lipase. The functionalised enantioenriched diastereoisomers obtained are important building blocks in organic synthesis.
  • Idioma: Inglês

Buscando em bases de dados remotas. Favor aguardar.