Synthesis of Amide Enol Carbamates and Carbonates through Cu(OTf)2-Catalyzed Reactions of Ynamides with t-Butyl Carbamates/Carbonates

被引：21

作者：

Han, Pan ^{[1
,2
]}

Mao, Zhuo-Ya ^{[1
]}

Li, Ming ^{[1
]}

Si, Chang-Mei ^{[1
]}

Wei, Bang-Guo ^{[1
]}

Lin, Guo-Qiang ^{[3
]}

机构：

[1] Fudan Univ, Sch Pharm, Dept Nat Med, Shanghai 201203, Peoples R China

[2] China West Normal Univ, Coll Chem & Chem Engn, Nanchong 637002, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 07期

基金：

中国国家自然科学基金;

关键词：

KETENIMINIUM IONS; CARBOXYLIC-ACIDS; ESTERS; HYDROGENATION; HYDROAMINATION; ALKYLATION; ALKYNE;

D O I：

10.1021/acs.joc.9b03512

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly regioselective approach to access amide enol carbamates and carbonates 5a-5c', 7a -7h, and 9 was developed through Cu(OTf)(2)-catalyzed reactions of ynamides 4 with t-butyl carbamates 2 and 8 and t-butyl carbonates 6. Moreover, this strategy was successfully applied to generate amide enol carbamates 11a-11s and 14a-14f from imides 10 and 13 with ynamides through an N-Boc cleavage-addition ring-opening process. A range of substituents was amenable to this transformation, and the desired amide enol carbamates and carbonates were obtained in moderate to good yields.

引用

页码：4740 / 4752

页数：13

共 8 条

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TETRAHEDRON LETTERS, 2021, 67
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