Lipase-catalyzed kinetic resolution of (±)-mandelonitrile under conventional condition and microwave irradiation

The kinetic resolution of (±)-mandelonitrile was carried out using lipase from Candida antarctica under conventional condition (orbital shaker) and microwave irradiation in toluene, producing the (S)-mandelonitrile acetate with high selectivity (up to > 98% ee, enantiomeric excess). The unreacted...

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Bibliographic Details
Main Authors: Ribeiro,Sandra S., Oliveira,Julieta R. de, Porto,André L. M.
Format: Article in Journal/Newspaper
Language:English
Published: Sociedade Brasileira de Química 2012
Subjects:
kinetic resolution
Candida antarctica lipase
mandelonitrile
microwave irradiation
orbital shaker
Antarc*
Antarctica
Online Access:http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532012000700025
Description
Summary:The kinetic resolution of (±)-mandelonitrile was carried out using lipase from Candida antarctica under conventional condition (orbital shaker) and microwave irradiation in toluene, producing the (S)-mandelonitrile acetate with high selectivity (up to > 98% ee, enantiomeric excess). The unreacted (R)-mandelonitrile under microwave irradiation and conventional condition was partially converted into benzaldehyde by spontaneous chemical equilibrium. The (S)-mandelonitrile acetate under microwave irradiation was produced with 92% ee and 35% yield for 8 h of reaction. Conventional transesterification of (±)-mandelonitrile in an orbital shaker produced unreacted (R)-mandelonitrile (51% ee) and (S)-mandelonitrile acetate (98% ee) in accordance with Kazlauskas rule for 184 h of reaction.

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