Acylation of Nitronates: [3,3]-Sigmatropic Rearrangement of in Situ Generated N-Acyloxy,N-oxyenamines

被引：23

作者：

Kokuev, Aleksandr O. ^{[1
,2
]}

Antonova, Yulia A. ^{[1
,3
]}

Dorokhov, Valentin S. ^{[1
,2
]}

Golovanov, Ivan S. ^{[1
]}

Nelyubina, Yulia V. ^{[4
]}

Tabolin, Andrey A. ^{[1
]}

Sukhorukov, Alexey Yu. ^{[1
]}

Ioffe, Sema L. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Leninsky Prospect 47, Moscow 119991, Russia

[2] DI Mendeleev Univ Chem Technol Russia, Higher Chem Coll, Miusskaya Sq 9, Moscow 125047, Russia

[3] Moscow MV Lomonosov State Univ, Dept Chem, Leninskie Gory 1, Moscow 119991, Russia

[4] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, Vavilov Str 28, Moscow 119991, Russia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 18期

基金：

俄罗斯科学基金会;

关键词：

COPE REARRANGEMENT; ALPHA-OXYGENATION; INDOLE SYNTHESIS; N-OXIDES; ALDEHYDES; CYCLOADDITION; HYDROLYSIS; ION;

D O I：

10.1021/acs.joc.8b01652

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acylation of nitronates affords alpha-acyloxyoxime derivatives via an umpolung functionalization of the alpha-position. This transformation involves generation of hitherto unknown N-acyloxy,N-oxyenamines and their fast [3,3]-sigmatropic rearrangement driven by the cleavage of the weak N-O bond. The reaction has a broad scope, and it is regioselective in the case of nitronates possessing nonsymmetrically substituted alpha-positions. Application to the formal total synthesis of clausenamide and cis-clausenamide is presented.

引用

页码：11057 / 11066

页数：10

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