Carbonyl-Directed Addition of N-Alkylhydroxylamines to Unactivated Alkynes: Regio- and Stereoselective Synthesis of Ketonitrones

被引：4

作者：

Liu, Yilin ^{[1
,2
]}

Feng, Xiangqing ^{[2
]}

Liu, Yanyun ^{[1
]}

Ling, Hongwei ^{[1
]}

Li, Yuanxiang ^{[1
]}

Gong, Yingying ^{[1
]}

Cao, Lei ^{[1
]}

Chen, Liping ^{[1
]}

机构：

[1] Huaihua Univ, Coll Chem & Mat Engn, Inst Organ Synth, Huaihua 418008, Peoples R China

[2] Chinese Acad Sci, Inst Chem, CAS Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 02期

基金：

中国国家自然科学基金;

关键词：

COPE-TYPE HYDROAMINATION; VINYL NITRONES; CYCLOADDITIONS; OXIDATION; REAGENTS; HYDROXYLAMINES; REARRANGEMENT; ALKENES; ACIDS;

D O I：

10.1021/acs.orglett.8b03522

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of ketonitrones were synthesized in moderate to excellent yields with high chemo-, regio-, and stereoselectivity by using carbonyl-directed addition of N-alkylhydroxylamines to unactivated alkynes under mild conditions. The product diverisity could be controlled by the use of different bases, and EtN(n-Pr)(2) could promote the formation of ketonitrones while using EtONa as base led to indanone-derived nitrones. Control experiments indicated that the carbonyl group of the substrate acted as an H-bond acceptor except for an electron-withdrawing group, and conjugated enone skeleton accounted for the high selectivity.

引用

页码：382 / 386

页数：5

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