Palladium-catalyzed [4+2] cycloaddition of amido-tethered allylic carbonates with oxazol-5-(4H)-ones: synthesis of piperidine-2,6-dione derivatives

被引：11

作者：

Wang, Lan ^{[1
,2
]}

Liu, Min ^{[1
,2
]}

Lu, Mengxi ^{[1
,2
]}

Wang, Bo ^{[1
,2
]}

Han, Qihuan ^{[1
,2
]}

Jin, Jingrong ^{[1
,2
]}

Yu, Songcheng ^{[3
]}

Wu, Yongjun ^{[3
]}

Guo, Hongchao ^{[1
,2
]}

机构：

[1] China Agr Univ, Dept Chem, Beijing 100193, Peoples R China

[2] China Agr Univ, Innovat Ctr Pesticide Res, Beijing 100193, Peoples R China

[3] Zhengzhou Univ, Coll Publ Hlth, Zhengzhou 450001, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 03期

基金：

中国国家自然科学基金;

关键词：

METHYLIDENE-DELTA-VALEROLACTONES; VINYLETHYLENE CARBONATES; ANNULATION; ACCESS; CONSTRUCTION; LACTONES;

D O I：

10.1039/d2qo01783k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-catalyzed [4 + 2] cycloaddition of amido-tethered allylic carbonates with oxazol-5-(4H)-ones proceeded smoothly under mild reaction conditions to give various piperidine derivatives in moderate to excellent yields. The reaction worked via aza-1,4-dipole from in situ deprotonation of amido-tethered allyl carbonates.

引用

页码：813 / 818

页数：6

共 38 条

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[2] [3+2] Cycloaddition of Oxazol-5-(4H)-ones with Nitrones for Diastereoselective Synthesis of Isoxazolidin-5-ones
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[3] Base-Catalyzed Formal [3+2] Cycloaddition of Diazooxindoles with Oxazol-5-(4H)-ones
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[7] Formal [4+2] Cycloaddition of Vinyl Benzoxazinones with Oxazol-5-(4H)-ones for Diastereoselective Construction of 3,4-Disubstituted Dihydro-2(1H)-Quinolinones
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[8] Formal [5+2] Cycloaddition of Vinyloxiranes with Oxazol-5-(4H)-ones: A Facile Approach for Construction of Seven-Membered Lactones
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[9] Palladium-Catalyzed Divergent Imidoylative Cyclization of Multifunctionalized Isocyanides: Tunable Access to Oxazol-5(4H)-ones and Cyclic Ketoimines
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[10] Asymmetric Synthesis of 3,4-Dihydroquinolin-2-ones via a Stereoselective Palladium-Catalyzed Decarboxylative [4+2]-Cycloaddition
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