Introduction of the 4,4,4-Trifluorobut-2-ene Chain Exploiting a Regioselective Tsuji-Trost Reaction Catalyzed by Palladium Nanoparticles

被引：28

作者：

Hemelaere, Remy ^{[1
]}

Desroches, Justine ^{[1
]}

Paquin, Jean-Francois ^{[1
]}

机构：

[1] Univ Laval, Canada Res Chair Organ & Med Chem, CGCC, PROTEO,Dept Chim, Quebec City, PQ G1V 0A6, Canada

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 07期

基金：

加拿大创新基金会; 加拿大自然科学与工程研究理事会;

关键词：

OPTICALLY-ACTIVE 2-(TRIFLUOROMETHYL)ALKAN-1-OLS; TRIFLUOROMETHYL GROUP; SUBSTITUTION-REACTION; ASYMMETRIC-SYNTHESIS; ALLYLIC AMINATION; LIQUID-CRYSTALS; ISOMERIZATION; ENANTIOMERS; ALKENES; AMINES;

D O I：

10.1021/acs.orglett.5b00539

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-nanoparticle-catalyzed TsujiTrost reaction of 4,4,4-trifluorobut-2-en-1-yl acetate and ethyl(4,4,4-trifluorobut-2-en-1-yl)carbonate was accomplished with various nucleophiles including phenols, amines, and malonates. In the case of the phenols, isomerization of the double bond in the product (up to 20%) was observed as a side reaction. Further synthetic transformations including hydrogenation, the Diels-Alder reaction, and asymmetric dihydroxylation of a product were also examined.

引用

页码：1770 / 1773

页数：4

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