Catalyst-free Tandem 1,3-Dipolar Cycloaddition/Aldol Condensation: Diastereoselective Construction of the Azatetraquinane Skeleton

被引：10

作者：

Zimnitskiy, Nikolay S. ^{[1
]}

Denikaev, Andrey D. ^{[1
]}

Barkov, Alexey Y. ^{[1
]}

Kutyashev, Igor B. ^{[1
]}

Korotaev, Vladislav Y. ^{[1
]}

Sosnovskikh, Vyacheslav Y. ^{[1
]}

机构：

[1] Ural Fed Univ, Inst Nat Sci & Math, Ekaterinburg 620000, Russia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 13期

基金：

俄罗斯基础研究基金会;

关键词：

STABILIZED AZOMETHINE YLIDES; STEREOSELECTIVE-SYNTHESIS; NATURAL-PRODUCTS; CAGE COMPOUNDS; REGIO; NINHYDRIN; MULTICOMPONENT; CRINIPELLIN; DERIVATIVES; CURCUMIN;

D O I：

10.1021/acs.joc.0c01127

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The one-pot regioselective and diastereoselective method for the synthesis of 5-(het)aroyl-7-(het)-arylhexahydrobenzo[4,5]pentaleno[1,6a-b](thia)pyrrolizine-6,12-diones from accessible 1,5-di(het)arylpent-4-ene-1,3-diones or curcuminoids in 38-98% yield was developed. This reaction proceeds as a sequence of 1,3-dipolar cycloaddition of azomethine ylide generated in situ from ninhydrin and (thia)proline at the C=C bond of corresponding enedione, followed by spontaneous intramolecular aldol condensation and leads to the formation of an azatetraquinane scaffold.

引用

页码：8683 / 8694

页数：12

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