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
收藏
页码：8683 / 8694
页数：12
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