NHC-Catalyzed Intramolecular Redox Amidation for the Synthesis of Functionalized Lactams

被引：61

作者：

Thai, Karen ^{[1
]}

Wang, Li ^{[1
]}

Dudding, Travis ^{[2
]}

Bilodeau, Francois ^{[3
]}

Gravel, Michel ^{[1
]}

机构：

[1] Univ Saskatchewan, Dept Chem, Saskatoon, SK S7N 5C9, Canada

[2] Brock Univ, Dept Chem, St Catharines, ON L2S 3A1, Canada

[3] Boehringer Ingelheim Canada Ltd Res & Dev, Laval, PQ H7S 2G5, Canada

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 24期

基金：

加拿大自然科学与工程研究理事会; 加拿大创新基金会;

关键词：

RING EXPANSION; STEREOSELECTIVE-SYNTHESIS; ACTIVATED CARBOXYLATES; BOND-CLEAVAGE; GAMMA-LACTAMS; CARBENE; ALDEHYDES; GENERATION; CONVERSION; ESTERS;

D O I：

10.1021/ol102536s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A very efficient NHC-catalyzed lactamization reaction is reported. For most cases, the ring expansion reaction proceeds to cleanly furnish five- and six-membered N-Ts and N-Bn lactams, without the need for further purification. Evidence is presented suggesting a dual role for the stoichiometric base: (1) deprotonation of the triazolium precatalyst and (2) activation of the nitrogen leaving group through hydrogen bonding.

引用

页码：5708 / 5711

页数：4

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