Synthesis of chiral diamide ligands of tartaric acid and asymmetric addition of their tin complexes with benzaldehyde

Chin. J. Org. Chem. ›› 1994, Vol. 14 ›› Issue (2): 181-184. Previous Articles Next Articles

Original Articles

手性酒石酸二酰胺配体的合成及其锡络合物与苯甲醛的不对称加成

谭万会;张三奇;张生勇;冯锐

陕西省化学研究所;第四军医大学化学教研室;中国军事医学科学院

发布日期:1994-04-25

Synthesis of chiral diamide ligands of tartaric acid and asymmetric addition of their tin complexes with benzaldehyde

ZHANG SANQI;ZHANG SHENGYONG;FENG RUI

Published:1994-04-25

Abstract

(+)-N,N'-diphenyl tartaric acid diamide 2, (+)-N,N'-dibenzyl tartaric acid diamide 3, (+)-dicyclohexyl tartaric acid diamide 4, and (+)-N,N'-di-n-octyl tartaric acid diamide 5 are synthesized via the amidate of diethyl tartarate and corresponding amine, respectively. Chiral tin complexes 6 are also prepared by treatment of tin dichloride with 2 equiv. of doubly deprotonated tartaric acid diamide followed by addition of an allylic bromide. The reaction of 6 with benzaldehyde affords optically active homoallyic alcohols in 42～64％ yield and in 24～62％ e.e..

Key words: TIN COMPLEX, BENZALDEHYDE, CHIRAL REAGENT

CLC Number:

O621

Cite this article

ZHANG SANQI;ZHANG SHENGYONG;FENG RUI. Synthesis of chiral diamide ligands of tartaric acid and asymmetric addition of their tin complexes with benzaldehyde[J]. Chin. J. Org. Chem., 1994, 14(2): 181-184.

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手性酒石酸二酰胺配体的合成及其锡络合物与苯甲醛的不对称加成

Synthesis of chiral diamide ligands of tartaric acid and asymmetric addition of their tin complexes with benzaldehyde

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