The high stereoselectivity of the tandem sequence Diels-Alder reaction/Ireland-Claisen rearrangement starting from substituted O-(E)-Buta-1,3-dienyl ketene acetals and cyclic dienophiles

被引：4

作者：

Soldermann, Nicolas

Velker, Joerg

Neels, Antonia

Stoeckli-Evans, Helen

Neier, Reinhard

机构：

[1] Univ Neuchatel, Inst Chim, CH-2009 Neuchatel, Switzerland

[2] Novartis Inst BioMed Res Basel, CH-4056 Basel, Switzerland

[3] Actel Pharmaceut Ltd, Innovat Ctr, CH-4123 Allschwil, Switzerland

[4] Univ Neuchatel, Inst Microtech, CH-2009 Neuchatel, Switzerland

来源：

SYNTHESIS-STUTTGART | 2007年 / 15卷 / 15期

关键词：

cycloaddition; Diels-Alder reaction; rearrangement; stereoselectivity; tandem reaction;

D O I：

10.1055/s-2007-983773

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new tandem reaction leads to bicyclic cyclohexene derivatives with complete control of the relative configuration of the four chiral centers formed. The high diastereoselectivity is the consequence of an endo-selective Diels-Alder reaction followed by an Ireland-Claisen rearrangement that proceeds via a boat-like transition state.

引用

页码：2379 / 2387

页数：9

共 3 条

[1] A novel Ireland-Claisen rearrangement/Diels-Alder tandem reaction of propargylic acrylates with acyclic dienophiles
Yun-Xia Li
Yi-Lin Sheng
Bi-Song Zhang
Chinese Chemical Letters, 2013, 24 (02) : 137 - 139
[2] The novel sequence Diels-Alder reaction/Ireland-Claisen rearrangement applied to acyclic dienophiles: New insights into the selectivity of the Ireland-Claisen rearrangement
Velker, J
Roblin, JP
Neels, A
Tesouro, A
Stoeckli-Evans, H
Klaerner, FG
Gehrke, JS
Neier, R
SYNLETT, 1999, : 925 - 929
[3] A novel Ireland-Claisen rearrangement/Diels-Alder tandem reaction of propargylic acrylates with acyclic dienophiles
Li, Yun-Xia
Sheng, Yi-Lin
Zhang, Bi-Song
CHINESE CHEMICAL LETTERS, 2013, 24 (02) : 137 - 139

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