Copper-catalyzed multicomponent reaction of β-trifluoromethyl β-diazo esters enabling the synthesis of β-trifluoromethyl N,N-diacyl-β-amino esters

被引：4

作者：

Du, Youlong ^{[1
]}

Mei, Haibo ^{[1
]}

Makarem, Ata ^{[2
]}

Javahershenas, Ramin ^{[3
]}

Soloshonok, Vadim A. ^{[4
,5
]}

Han, Jianlin ^{[1
]}

机构：

[1] Nanjing Forestry Univ, Coll Chem Engn, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat Fo, Nanjing 210037, Peoples R China

[2] Univ Hamburg, Dept Chem, Martin Luther King Pl 6, D-20146 Hamburg, Germany

[3] Urmia Univ, Fac Chem, Dept Organ Chem, Orumiyeh, Iran

[4] Univ Basque Country UPV EHU, Fac Chem, Dept Organ Chem 1, Paseo Manuel Lardizabal 3, San Sebastian 20018, Spain

[5] Basque Fdn Sci, IKERBASQUE, Alameda Urquijo 36-5,Plaza Bizkaia, Bilbao 48011, Spain

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 20卷

关键词：

beta-carbonyl diazo; copper catalyst; fluoroalkyl diazo; Mumm rearrangement; unsymmetrical beta-diacylamino esters; CARBOXYLIC-ACIDS; AMINO-ACIDS; FLUORINE; TRANSAMINATION; ESTERIFICATION; CYCLOADDITION; REARRANGEMENT; DERIVATIVES; GENERATION;

D O I：

10.3762/bjoc.20.21

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient multicomponent reaction of newly designed beta-trifluoromethyl beta-diazo esters, acetonitrile, and carboxylic acids via an interrupted esterification process under copper -catalyzed conditions has been developed, which affords various unsymmetrical beta-tri- fluoromethyl N,N-diacyl-beta-amino esters in good to excellent yields. The reaction features mild conditions, a wide scope of beta -amino esters and carboxylic acids, and also applicability to large-scale synthesis, thus providing an efficient way for the synthesis of beta-tri- fluoromethyl beta-diacylamino esters. Furthermore, this reaction represents the first example of a Mumm rearrangement of beta-trifluoro- methyl beta-diazo esters.

引用

页码：212 / 219

页数：8

共 61 条

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