Dimethylaluminum methide complex Tf2CHAIMe2:: an effective catalyst for Diels-Alder reaction of α,β-unsaturated lactone derivatives with cyclopentadiene

被引：18

作者：

Yanai, Hikaru ^{[1
]}

Takahashi, Arata ^{[1
]}

Taguchi, Takeo ^{[1
]}

机构：

[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, Hachioji, Tokyo 1920392, Japan

来源：

TETRAHEDRON | 2007年 / 63卷 / 49期

关键词：

Lewis acid; Bis(trifluoromethanesulfonyl)methane; Diels-Alder reaction; alpha; beta-Unsaturated lactones;

D O I：

10.1016/j.tet.2007.09.061

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lewis acid derived by mixing Tf2CH2 and Me(3)AI was found to be an effective catalyst system for the catalytic DA reaction of less reactive a, P-unsaturated lactone derivative with cyclopentadiene (CP). In this catalyst system, Tf(2)CHAIMe(2) is an active species and an excess amount of Me3AI plays an important role to lower the catalyst loading. Substituent effect of the lactone framework on pi-facial selectivity was also examined. In the reactions of both gamma-substituted 5-membered lactone derivatives and gamma- or delta-methylated 6-membered lactone derivatives with CP, selective attack on the anti face of gamma- or delta-substituent was observed. On the other hand, in the cases of gamma- or epsilon-methylated 7-membered lactone derivatives, CP favorably attacked on the syn face. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：12149 / 12159

页数：11

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