Acta Chimica Sinica ›› 1987, Vol. 45 ›› Issue (3): 287-290. Previous Articles     Next Articles

Original Articles

胶束模拟酶的研究2:手性胶束中硫醚氧化为亚砜的不对称诱导

范伟强;周青山;沈积慧;吕萍;张永敏   

  1. 杭州大学化学系
  • 发布日期:1987-03-15

The study of micellar imitating enzyme model 2: asymmetric induction of the oxidation of prochiral sulfide in chiral micellar systems

FAN WEIQIANG;ZHOU QINGSHAN;SHEN JIHUI;LU PING;ZHANG YONGMIN   

  • Published:1987-03-15

Chiral surfactants S-(-)-, R-(+)-PhCHMeN+Me2(CH2)11MeBr- and D-PhCH(OH)CHMeN+Me2(CH2)11MeBr- were synthesized from (+)- and (-)-a-Me benzylamine and natural ephedrine. The chiral micellar systems consisting of these surfactants can be used as the most simple model of enzyme and studied in the stereospecific catalysis. In the chiral micellar systems chiral sulfoxides, PhSOR (R = alkyl) can be obtained by the asym. oxidation of sulfides with NaIO4 or H2O2, enantiomer excess (e.e.%) amts. to 2-8%. This is an example of asym. induction of the oxidation of prochiral sulfide in micellar system. The relation of the structure of surfactants and asym. induction was also discussed.

Key words: OXIDATION, SULFOXIDE, SURFACTANTS, SULFUR ETHER, ENANTIOMORPH, STEREOSELECTIVITY, MICELLAR SOLUTION, CONFIGURATION, BENZENEMETHANAMINE P, CHIRALITY

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