Carbonyl-yne reactions of 3,3,3-trifluoropyruvates

被引：19

作者：

Golubev, AS ^{[1
]}

Sergeeva, NN ^{[1
]}

Hennig, L ^{[1
]}

Kolomiets, AF ^{[1
]}

Burger, K ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2003年 / 59卷 / 09期

关键词：

carbonyl-yne reaction; 2,3-allenols; 3,3,3-trifluoropyruvates; fluoroalkyl-substituted 2,5-dihydrofurans;

D O I：

10.1016/S0040-4020(03)00084-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of trifluoromethyl-containing 2,3-allenols via carbonyl-yne reaction of 3,3,3-trifluoropyruvates with acetylenes is described. In the presence of MgBr2.Et2O the reaction of methyl trifluoropyruvate with hex-1-yne proceeds diastereoselectively. Trifluoromethyl-substituted 2,3-allenols can be stereoselectively transformed into trifluoromethyl-substituted 2,5-dihydrofurans on treatment with AgNO3. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：1389 / 1394

页数：6

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