Highly stereoselective synthesis of 6-perfluoroalkyl-6-fluoroalka-2,3,5(Z)-trienols through carbometallation-elimination of 5-perfluoroalkyl-substituted 4(E)-alken-2-ynols with Grignard reagents

被引：5

作者：

Ma, Zhichao ^{[1
]}

Zeng, Rong ^{[1
]}

Yu, Yihua ^{[2
]}

Ma, Shengming ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Lab Mol Recognit & Synth, Hangzhou 310027, Zhejiang, Peoples R China

[2] E China Normal Univ, Dept Phys, Shanghai Key Lab Funct Magnet Resonance Imaging, Shanghai 200062, Peoples R China

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 47期

基金：

中国国家自然科学基金;

关键词：

ELECTROLYTIC PARTIAL FLUORINATION; RADICAL-ADDITION REACTION; PERFLUOROALKYL IODIDES; GEM-DIFLUOROALLENYL; CATALYZED REACTIONS; EFFICIENT SYNTHESIS; ORGANIC-COMPOUNDS; COUPLING REACTION; ALLENES; FLUOROOLEFINS;

D O I：

10.1016/j.tetlet.2009.09.003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly regio- and stereoselective sequential carbometallation and Z-selective beta-elimination reaction of 5-perfluoroalkyl-4(E)-en-2-ynols with Grignard reagents in Et2O has been developed to afford various 6-perfluoroalkyl-6-fluoroalka-2,3,5(Z)-trienols in good to excellent yields Primary or secondary alkyl or aryl Grignard reagents may be used to introduce the R-2 group to the 2-position of the starting materials referring to the hydroxyl group A mechanism for this transformation has been proposed. (C) 2009 Elsevier Ltd. All rights reserved

引用

页码：6472 / 6475

页数：4

共 3 条

[1] A facile stereoselective synthesis of 2-perfluoroalkyl-3a,4,5, 6-tetrahydroimidazo[1,5-b]isoxazoles
Lu, Lei
Cao, Weiguo
Chen, Jie
Zhang, Hui
Zhang, Jiaping
Chen, Huiyun
Wei, Jiamei
Deng, Hongmei
Shao, Min
JOURNAL OF FLUORINE CHEMISTRY, 2009, 130 (03) : 295 - 300
[2] STUDIES ON THE APPLICATION OF ELEMENTOORGANIC COMPOUNDS OF THE 5TH AND 6TH GROUPS IN ORGANIC SYNTHESES .33. REACTIONS OF CYANOMETHYLENETRIPHENYLPHOSPHORANE AND ARSORANE WITH METHYL PERFLUORO-2-ALKYNOATES AND STEREOSELECTIVE SYNTHESIS OF METHYL 3-PERFLUOROALKYL-4-CYANO-3-BUTENOATES
DING, WY
PU, JQ
ZHANG, PS
ACTA CHIMICA SINICA, 1987, 45 (01) : 47 - 51
[3] Unusual regioselectivity of Pd(0)-catalyzed coupling reaction of electron-deficient alkenyl halides with allenic/propargylic zinc reagents. Highly selective synthesis of 6-phenylhex-5-yn-2(or 3)-enoates/enitrile and 4-phenyl-6-substituted-hexa-2,4,5-trienoates
Ma, SM
Zhang, AB
Yu, YH
Xia, W
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (08): : 2287 - 2291

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