A green route to enantioenriched (S)-arylalkyl carbinols by deracemization via combined lipase alkaline-hydrolysis/Mitsunobu esterification
(2013) Tetrahedron: Asymmetry — Vol. 24, n° 5-6, p. 290-296 (2013)
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- Herein we report results of the chemoenzymatic deracemization of a range of secondary benzylic acetates 1a-9a via a sequence of hydrolysis with CAL-B lipase in non-conventional media, combined with esterification of the recovered alcohol according to the Mitsunobu protocol following an enzymatic kinetic resolution (KR). The KR of racemic acetates 1a-9a via an enzymatic hydrolysis, with CAL-B lipase and Na2CO3, in non-aqueous media was optimized and gave high selectivities (E ≫ 200) at good conversions (C >49%) for all of the substrates studied. This method competes well with the traditional one performed in a phosphate buffer solution. The deracemization using Mitsunobu inversion gave the (S)-acetates in moderate to excellent enantiomeric excess 75% < ee < 99%, in acceptable isolated yields 70% < yield < 89%, and with some variations according to the acetate structure. © 2013 Elsevier Ltd. All rights reserved.
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Houiene, Z., Merabet-Khelassi, M., Bouzemi, N., Riant, O., & Aribi-Zouioueche, L. (2013). A green route to enantioenriched (S)-arylalkyl carbinols by deracemization via combined lipase alkaline-hydrolysis/Mitsunobu esterification. Tetrahedron: Asymmetry, 24(5-6), 290-296. https://doi.org/10.1016/j.tetasy.2013.01.020 (Original work published 2013)