The effect of catalytic amount of calcium hydride and silica gel on Sharpless asymmetric epoxidation

Chin. J. Org. Chem. ›› 1992, Vol. 12 ›› Issue (1): 29-34. Previous Articles Next Articles

Original Articles

催化量的氧化钙-硅胶对Sharpless烯丙醇不对称环氧化的影响

王志民;周维善

中国科学院上海有机化学研究所

发布日期:1992-02-25

The effect of catalytic amount of calcium hydride and silica gel on Sharpless asymmetric epoxidation

WANG ZHIMIN;ZHOU WEISHAN

Published:1992-02-25

Abstract

The reaction time of asym. epoxidn. of allylic al. was drastically reduced whereas the enantioselectivity increased when a catalytic amount of CaH2 and SiO2 was present in the Sharpless reagent. Transition state studies indicated a SN2 mechanism, in which the interaction between Ca2+ and O in the peroxide species accelerated the O-O bond cleavage and increased the reaction rate. The adsorbed Ca2+ on SiO2 prevented the decrease in enantioselectivity.

Key words: TARTARIC ACID P, EPOXIDATION REACTION, ASYMMETRY, TITANIUM COMPLEX, CALCIUM HYDRIDE, PROPOXY GROUP, SILICA GEL, METAL HYDRIDE, ALLYL ALCOHOL

CLC Number:

O621

Cite this article

WANG ZHIMIN;ZHOU WEISHAN. The effect of catalytic amount of calcium hydride and silica gel on Sharpless asymmetric epoxidation[J]. Chin. J. Org. Chem., 1992, 12(1): 29-34.

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催化量的氧化钙-硅胶对Sharpless烯丙醇不对称环氧化的影响

The effect of catalytic amount of calcium hydride and silica gel on Sharpless asymmetric epoxidation

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