First stereocontrolled acetylation of a hydroxypropargylpiperidone by lipase CALB |
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Authors: | Gliseida Z Melgar Edison P Wendler Alcindo A dos Santos André LM Porto |
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Institution: | 1. Instituto de Química de São Carlos, Universidade de São Paulo, Av. Trabalhador São-carlense, 400, CEP 13560-970 São Carlos, SP, Brazil;2. Departamento de Química, Universidade Federal de São Carlos, Rodovia Washington Luís, km 235, CEP 13565-905 São Carlos, SP, Brazil;3. Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CEP 05508-000 São Paulo, SP, Brazil |
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Abstract: | 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. |
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