Functionalized analogues of Troger's base: scope and limitations of a general synthetic procedure and facile, predictable method for the separation of enantiomers

被引：51

作者：

Didier, Delphine ^{[1
]}

Tylleman, Benoit ^{[1
]}

Lambert, Natacha ^{[1
]}

Velde, Christophe M. L. Vande ^{[1
]}

Blockhuys, Frank ^{[2
]}

Collas, Alain ^{[2
]}

Sergeyev, Sergey ^{[1
]}

机构：

[1] Univ Libre Bruxelles, Lab Chim Polymeres, CP 206-01,Blvd Triomphe, B-1050 Brussels, Belgium

[2] Univ Instelling Antwerp, Dept Chem, B-2610 Antwerp, Belgium

来源：

TETRAHEDRON | 2008年 / 64卷 / 27期

关键词：

Troger's base; enantioseparation; Whelk O1; anilines;

D O I：

10.1016/j.tet.2008.04.111

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A major stumbling block in the applications of enantiomerically pure Troger's base analogues is their poor availability. We have therefore developed a facile method for the enantioseparation of functionalized Troger's base analogues possessing various substitution patterns. The systematic separation of a library comprising 36 representatives on the commercially available Whelk O1 chiral stationary phase provided valuable information on structure-enantioselectivity relationships. A mechanistic explanation of observed relationships allows one to predict whether or not enantioseparation of a given, perhaps yet unknown derivative of Troger's base will be feasible. in addition, we provide a detailed report on the scope and limitations of the general synthetic protocol employing anilines and paraformaldehyde in CF3COOH, as well as some considerations concerning the mechanism of formation of Troger's base analogues. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：6252 / 6262

页数：11

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