Synthesis of 1,3-Bis(9-O-quininyl)isophthalate and Its Preliminary Study in the Asymmetric Dihydroxylation of Olefins

Chem. J. Chinese Universities ›› 1999, Vol. 20 ›› Issue (6): 900.

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Synthesis of 1,3-Bis(9-O-quininyl)isophthalate and Its Preliminary Study in the Asymmetric Dihydroxylation of Olefins

ZHANG Ke-Sheng, SUN Jun-Tan, HE Bing-Lin

Institute of Polymer Chemistry, the State Key Laboratory of Functional Polymer Materials for Adsorption and Separation, Nankai University, Tianjin, 300071

Received:1998-10-10 Online:1999-06-24 Published:1999-06-24

Abstract

Abstract: 1,3-Bis(9-O-quininyl)isophthalate(BQIP) was synthesized from quinine and isophthaloyl dichloride directly. High enantioselectivity and reactivity have been achieved in asymmetric dihydroxylation of transstilbene using BQIP as catalyst(optical yield: 99%), and lower enantioselectivity to styrene was obtained(optical yield: 84.3%). It can be deduced that the chiral cage in BQIP could bind transstilbene more firmly than styrene. Low reaction temperature brought about higher enantioselectivity than that of the high one.

Key words: 1,3-Bis(9-O-quininyl)isophthalate(BQIP), Asymmetric dihydroxylation of olefins, Catalysis olefin

CLC Number:

O626.21

TrendMD:

ZHANG Ke-Sheng, SUN Jun-Tan, HE Bing-Lin . Synthesis of 1,3-Bis(9-O-quininyl)isophthalate and Its Preliminary Study in the Asymmetric Dihydroxylation of Olefins[J]. Chem. J. Chinese Universities, 1999, 20(6): 900.

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Synthesis of 1,3-Bis(9-O-quininyl)isophthalate and Its Preliminary Study in the Asymmetric Dihydroxylation of Olefins

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