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有机化学
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有机化学 ›› 1986, Vol. 6 ›› Issue (5): 386-388. 上一篇    下一篇

研究论文

胶束模似酶的研究1.手性胶束中酮的不对称还原

周青山;范伟强;张永敏;吴华悦;张存敏   

  1. 杭州大学化学系
  • 发布日期:1986-10-25

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

ZHOU QINGSHAN;FAN WEIQIANG;ZHANG YONGMIN;WU HUAYUE;ZHANG CUNMIN   

  • Published:1986-10-25

PDF

359

被引次数

6

在(+)和(-)-N-十六烷基-N,N-二甲基-α-苯乙铵溴化物(1a和1b)及N-十二烷基-N,N-二甲基麻黄素溴化铵(2)等表面活性剂形成的手性胶束溶液中,以NaBH~4还原潜手性的苯基烷基酮可诱导出不对称中心,生成旋光性的醇.e.e.%最大值可达8.6%.产物醇的构型取决于所 用胶束的构型,对只有一个手性中心的胶束1a和1b,.产物构型和胶束相反.手性胶束结构对产物的光学得率影响较大.

关键词: 苯乙胺 P, 表面活性剂, 溴化物, 对映体, 还原反应, 酮, 胶束溶液, 手征性, 模拟酶, 麻黄素

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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