Stereoselective Synthesis of Terminal Monofluoroalkenes from Trifluoromethylated Alkenes

被引：38

作者：

Poutrel, Pauline ^{[1
]}

Pannecoucke, Xavier ^{[1
]}

Jubault, Philippe ^{[1
]}

Poisson, Thomas ^{[1
,2
]}

机构：

[1] Normandie Univ, INSA Rouen, UNIROUEN, CNRS,COBRA,UMR 6014, F-76000 Rouen, France

[2] Inst Univ France, F-75231 Paris, France

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 12期

关键词：

PALLADIUM-CATALYZED SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; GEM-DIFLUOROALKENES; FLUORINE; OLEFINATION; ANALOGS; 3,3-DIFLUOROPROPENES; CYCLOPROPANATION; DERIVATIVES; INHIBITORS;

D O I：

10.1021/acs.orglett.0c01701

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein we report the hydrodefluorination reaction of trifluoromethylated alkenes to access terminal monofluoroalkenes. The use of LiAlH4 allowed the stereoselective synthesis of the terminal monofluoroalkenes in good to excellent yields with good to excellent diastereoselectivities. Mechanistic studies suggested a hydroalumination reaction followed by a stereoselective fluoride elimination.

引用

页码：4858 / 4863

页数：6

共 68 条

[21] Fluorination of Boronic Acids Mediated by Silver(I) Triflate [J].

Furuya, Takeru ;

Ritter, Tobias .

ORGANIC LETTERS, 2009, 11 (13) :2860-2863

[22] Applications of Fluorine in Medicinal Chemistry [J].

Gillis, Eric P. ;

Eastman, Kyle J. ;

Hill, Matthew D. ;

Donnelly, David J. ;

Meanwell, Nicholas A. .

JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (21) :8315-8359

[23]

Groult H., 2017, Modern Synthesis Processes and Reactivity of Fluorinated Compounds

[24] Exploiting a Difference in Leaving Group Ability: An Approach to β-Substituted Monofluoroalkenes Using gem-Chlorofluoropropenes [J].

Hamel, Jean-Denys ;

Cloutier, Melissa ;

Paquin, Jean-Francois .

ORGANIC LETTERS, 2016, 18 (08) :1852-1855

[25] Disubstituted Bis-THF Moieties as New P2 Ligands in Nonpeptidal HIV-1 Protease Inhibitors (II) [J].

Hohlfeld, Konrad ;

Wegner, Joerg Kurt ;

Kesteleyn, Bart ;

Linclau, Bruno ;

Unge, Johan .

JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (09) :4029-4038

[26] Stereoselective Synthesis of Z Fluoroalkenes through Copper-Catalyzed Hydrodefluorination of gem-Difluoroalkenes with Water [J].

Hu, Jiefeng ;

Han, Xiaowei ;

Yuan, Yu ;

Shi, Zhuangzhi .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (43) :13342-13346

[27] Catalytic Asymmetric Synthesis of α,α-Difluoromethylated and α-Fluoromethylated Tertiary Alcohols [J].

Huang, Wei-Sheng ;

Delcourt, Marie-Leonie ;

Pannecoucke, Xavier ;

Charette, Andre B. ;

Poisson, Thomas ;

Jubault, Philippe .

ORGANIC LETTERS, 2019, 21 (18) :7509-7513

[28] General Catalytic Enantioselective Access to Monohalomethyl and Trifluoromethyl Cyclopropanes [J].

Huang, Wei-Sheng ;

Schlinquer, Claire ;

Poisson, Thomas ;

Pannecoucke, Xavier ;

Charette, Andre B. ;

Jubault, Philippe .

CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (41) :10339-10343

[29] Data-Mining for Sulfur and Fluorine: An Evaluation of Pharmaceuticals To Reveal Opportunities for Drug Design and Discovery [J].

Ilardi, Elizabeth A. ;

Vitaku, Edon ;

Njardarson, Jon T. .

JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (07) :2832-2842

[30] Stereoselective synthesis of β-fluoroenyne by the reaction of gem-difluoroalkenes with terminal alkynes [J].

Jin, Guanyi ;

Zhang, Juan ;

Wu, Wei ;

Cao, Song .

JOURNAL OF FLUORINE CHEMISTRY, 2014, 168 :240-246

← 1 2 3 4 5 6 7 →