Stereospecific Synthesis of Cyclohexenone Acids by [3,3]-Sigmatropic Rearrangement Route

被引：2

作者：

Eronen, Aleksi ^{[1
]}

Nieger, Martin ^{[1
]}

Kajander, Tommi A. ^{[2
]}

Repo, Timo ^{[1
]}

机构：

[1] Univ Helsinki, Dept Chem, Helsinki 00014, Finland

[2] Univ Helsinki, Inst Biotechnol, Helsinki 00014, Finland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 18期

关键词：

28;

D O I：

10.1021/acs.joc.3c00757

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we report a modular synthetic method for the preparation of diaryl-substituted cyclohexenone acids starting from phenyl pyruvate and suitable enones. When the reaction is carried out in alkaline tert-butanol or toluene solutions in microwave-assisted conditions mainly anti configuration products are obtained with up to 86% isolated yield. However, when the reaction is carried out in alkaline water, a mixture of products with anti and syn conformations is obtained with up to 98% overall isolated yield. Mechanistically the product with anti conformation forms by a hemiketal-oxy-Cope type [3,3]-sigmatropic rearrangement-intramolecular aldol condensation route and syn product by an intermolecular aldol condensation-electrocyclization (disrotatory type) route.

引用

页码：12914 / 12923

页数：10

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