Cu-Catalyzed Redox-Neutral Ring Cleavage of Cycloketone O-Acyl Oximes: Chemodivergent Access to Distal Oxygenated Nitriles

被引：104

作者：

Ai, Wenying ^{[1
,2
]}

Liu, Yaqian ^{[3
]}

Wang, Qian ^{[2
]}

Lu, Zhonglin ^{[1
]}

Liu, Qiang ^{[2
]}

机构：

[1] Beijing Normal Univ, Coll Chem, Beijing 100875, Peoples R China

[2] Tsinghua Univ, Dept Chem, CBMS, Beijing 100084, Peoples R China

[3] Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 02期

关键词：

CYCLOBUTANOLS REGIOSPECIFIC SYNTHESIS; BOND-CLEAVAGE; OPENING CHLORINATION; TERT-CYCLOBUTANOLS; CARBOACYLATION; ACTIVATION; CYCLOADDITION; CYCLOALKANOLS; DERIVATIVES; GENERATION;

D O I：

10.1021/acs.orglett.7b03707

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A chemodivergent copper-catalyzed ring opening of cyclokettoe oximes via radical-mediated C-C bond cleavage under redox-neutral conditions is described. This method allows the divergent synthesis of gamma- and delta-acyloxylatect alkoxylated, and hydroxylated nitrites while avoiding the use of toxic cyanide reagents. Moreover, these reactions proceed under very mild conditions with good functional group tolerance. Notably, ring-opening reactions of the less-strained substrate cyclopentanone oxinie also proceeded well under the established conditions.

引用

页码：409 / 412

页数：4

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