Asymmetric isomerisation of a cyclic diene:: a comparative study of BINAP and BIPNOR-rhodium(I) catalysts

被引：32

作者：

Faitg, T

Soulié, J

Lallemand, JY

Mercier, F

Mathey, F ^{[1
]}

机构：

[1] Ecole Polytech, DCPH, UMR 7653 CNRS, Lab Heteroelements & Coordinat, F-91128 Palaiseau, France

[2] Ecole Polytech, DSCO, UMR 7652 CNRS, Organ Synth Lab, F-91128 Palaiseau, France

来源：

TETRAHEDRON | 2000年 / 56卷 / 01期

关键词：

asymmetric isomerisation; cyclic dienes; enantiomeric excess;

D O I：

10.1016/S0040-4020(99)00778-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The asymmetric isomerisation of 5,7-dibenzyloxy-6-(triallcylsilyloxy) cyclohepta-1,3-diene 1 to the corresponding 1,6-dibenzyloxy-7-(triallcylsilyloxy) cyclohepta-1,3-diene 2 can be accomplished at 90 degrees C in a 75/25 mixture of toluene and DME in the presence of a [Rh(BIPNOR)(cod)](+) catalyst with 92% ee. A much lower ee is observed with BINAP. In both cases, the observed ee's increase with temperature. A mechanism involving an eta(5)-pentadienyl-rhodium complex is proposed. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：101 / 104

页数：4

共 11 条

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