Origins of micellar diastereoselectivity

RA Moss, YCP Chiang, Y Hui

Index: Moss, Robert A.; Chiang, Yuan-Ching P.; Hui, Yongzheng Journal of the American Chemical Society, 1984 , vol. 106, # 24 p. 7506 - 7513

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Citation Number: 21

Abstract

Abstract: Thiol-functionalized surfactant micelles (n-C12H25NfMe2CH2CH2SH, CI-) were used to cleave Z-TrpPro p-nitrophenyl dipeptide esters. Marked kinetic diastereoselectivity was observed in these reactions. For example at pH 8 and concentrations (-6-7) XM, the micellar thiol cleaved the LL substrate 5-6 times more rapidly than its DL diastereomer. This kinetic diastereoselectivity was shown to develop at surfactant concentrations-5 XM), Le., ...