Study on micellar imitate enzyme model 1. asymmetric reduction of ketones in chiral micellar systems

Abstract

Chiral surfactants S(-)- and R(+)-PhCHMeN+Me2(CH2)15Me Br-, and (-)-PhCH(OH)CHMeN+Me2(CH2)11Me Br- were prepared by the quaternization of the corresponding a-methylbenzylamines or (-)-ephedrine with C16H33Br or C12H25Br. Prochiral phenyl alkyl ketones PhCOR (R = Me, Et, Pr or iso-Pr) were reduced by NaBH4 in micellar systems containing these chiral surfactants to give the corresponding chiral carbinols. The configuration of the carbinols was opposite that of the surfactant used.

Key words: PHENYLETHYLAMINE P, SURFACTANTS, BROMIDE, ENANTIOMORPH, REDUCTION REACTION, KETONE, MICELLAR SOLUTION, CHIRALITY, MODELS OF ENZYME, EPHEDRINE

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Cite this article

ZHOU QINGSHAN;FAN WEIQIANG;ZHANG YONGMIN;WU HUAYUE;ZHANG CUNMIN. Study on micellar imitate enzyme model 1. asymmetric reduction of ketones in chiral micellar systems[J]. Chin. J. Org. Chem., 1986, 6(5): 386-388.

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