Domino reactions with fluorinated five-membered heterocycles -: Syntheses of trifluoromethyl substituted butenolides and γ-ketoacids

被引：12

作者：

Burger, K ^{[1
]}

Hennig, L

Fuchs, A

Greif, D

Spengler, J

Albericio, F

机构：

[1] Univ Leipzig, Dept Organ Chem, D-04103 Leipzig, Germany

[2] Hsch Zittau Gorlitz, Fachbereich Math & Nat Wissensch, D-02763 Zittau, Germany

[3] Inst Recerca Biomed Barcelona, Barcelona 08028, Spain

来源：

MONATSHEFTE FUR CHEMIE | 2005年 / 136卷 / 10期

关键词：

2-fluoro-3-trifluoromethylthiophenes; 2-fluoro-3-trifluoromethylfurans; trifluoromethyl substituted butenolides; alpha-trifluoromethyl-gamma-keto acids; domino reactions;

D O I：

10.1007/s00706-005-0366-z

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new approach to trifluoromethyl substituted butenolides and their thioanalogues is described starting from 2-fluoro-3-trifluoromethylfurans and -thiophenes, respectively. The reaction sequence includes three steps - nucleophilic displacement reaction. Claisen, and finally Cope rearrangement - which can be run as domino reaction. A modification of the domino reaction (transesterification instead of Cope rearrangement) provides a concise access to alpha-trifluoromethyl-gamma-ketoacids.

引用

页码：1763 / 1779

页数：17

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