Rhodium-catalysed asymmetric ring opening reactions with carboxylate nucleophiles

被引：77

作者：

Lautens, M ^{[1
]}

Fagnou, K ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada

来源：

TETRAHEDRON | 2001年 / 57卷 / 24期

基金：

加拿大自然科学与工程研究理事会;

关键词：

asymmetric catalysis; rhodium; carboxylate;

D O I：

10.1016/S0040-4020(01)00351-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have developed an asymmetric ring opening reaction of oxabenzonorbornadiene with carboxylate nucleophiles to generate enantiomerically enriched hydronaphthalene products containing an allylic carboxylate moiety. These reactions occur in good yield and excellent enantioselectivity (>90% ee). The allylic carboxylate functionality was found to be stable towards reaction with the rhodium catalyst under the reaction conditions. In order to obtain these results, two advancements were required. First, the use of protic additives was necessary for good reactivity. Second, the exchange of the halide Ligand on the catalyst from chloride to iodide was required to obtain high ee. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：5067 / 5072

页数：6

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