Resolution of racemic carboxylic acid derivatives by Ti-TADDOLate mediated esterification reactions - A general method for the preparation of enantiopure compounds

被引：104

作者：

Seebach, D ^{[1
]}

Jaeschke, G ^{[1
]}

Gottwald, K ^{[1
]}

Matsuda, K ^{[1
]}

Formisano, R ^{[1
]}

Chaplin, DA ^{[1
]}

Breuning, M ^{[1
]}

Bringmann, G ^{[1
]}

机构：

[1] UNIV WURZBURG,INST ORGAN CHEM,D-97074 WURZBURG,GERMANY

来源：

TETRAHEDRON | 1997年 / 53卷 / 22期

关键词：

D O I：

10.1016/S0040-4020(97)00456-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Lewis-acid mediated transfer of an alkoxide ligand from the chiral ligand sphere of Ti-TADDOLates 1 to cyclic carboxylic acid derivatives is described. The kinetic resolution of dioxolanones, azlactones and biaryl lactones by the Ti-TADDOLates affords, after recrystallization, ester products in highly enantioenriched form (er greater than or equal to 97:3). The enantiomer-differentiating ring-opening of a chiral cyclic anhydride by a Ti-TADDOLate leads highly enantioselectively to two constitutional isomers. (C) 1997 Elsevier Science Ltd.

引用

页码：7539 / 7556

页数：18

共 69 条

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