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

从(+)-和(-)-α-甲基苄胺和天然麻黄素(ephedrine)合成三个手性表面活性剂,由这些表面活性剂组成的手性胶团体系可用作最简单的酶模型和立体专一性催化的研究,在手性胶团体系中,手性亚砜可以用NaIO4或H2O2不对称氧化硫醚而获得,讨论了表面活性剂结构与不对称诱导之间的关系.

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

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.