Stereoselective Synthesis of α-Trifluoromethyl Enones by AuI/CuI-Co-Catalyzed Tandem 1,3-Acyloxy Migration/Trifluoromethylation Reaction of Propargyl Acetates

被引：14

作者：

Ji, Yun-Long ^{[1
]}

Lin, Jin-Hong ^{[1
]}

Xiao, Ji-Chang ^{[1
]}

Gu, Yu-Cheng ^{[2
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

[2] Syngenta, Jealotts Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 35期

关键词：

Synthetic methods; Trifluoromethylation; Gold; Copper; Stereooselectivity; Enones; COPPER-MEDIATED TRIFLUOROMETHYLATION; EFFICIENT SYNTHESIS; GOLD; REARRANGEMENT; FLUORINE; ESTERS; OXYTRIFLUOROMETHYLATION; COMPLEXES; ALLENES; ALKYNES;

D O I：

10.1002/ejoc.201403115

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Au-I/Cu-I-co-catalyzed tandem 1,3-acyloxy migration/trifluoromethylation reaction of propargyl esters to give -trifluoromethyl enones in moderate yields and with excellent stereoselectivity is described. It is proposed that the reaction proceeds through the 1,3-acyloxy migration of the propargyl esters catalyzed by Au-I to produce an allenic intermediate, followed by its trifluoromethylation to give the final product.

引用

页码：7948 / 7954

页数：7

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