Base-mediated diastereoselective [4+3] annulation of in situ generated ortho-quinone methides with C, N-cyclic azomethine imines

被引：33

作者：

Xu, Jianfeng ^{[1
]}

Yuan, Shiru ^{[1
]}

Peng, Jingyi ^{[1
]}

Miao, Maozhong ^{[1
]}

Chen, Zhengkai ^{[1
]}

Ren, Hongjun ^{[1
]}

机构：

[1] Zhejiang Sci Tech Univ, Dept Chem, Hangzhou 310018, Zhejiang, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 36期

基金：

中国国家自然科学基金;

关键词：

ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; ISATIN-DERIVED KETIMINES; BIOMIMETIC SYNTHESES; MELDRUMS ACID; CARBENE; ACCESS; CATALYST; YLIDES; ENALS;

D O I：

10.1039/c7ob01783a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient [4 + 3] annulation of 2-(1-tosylalkyl) phenols with C, N-cyclic azomethine imines via in situ generation of ortho-quinone methides (o-QMs) under mild basic reaction conditions is disclosed, furnishing biologically interesting seven-membered heterocyclic compounds with moderate to good yields and excellent diastereoselectivities. A gram-scale reaction is performed to demonstrate the potential in industrial application and two transition states are proposed to rationalize the outstanding diastereoselectivity.

引用

页码：7513 / 7517

页数：5

共 29 条

[1] Catalytic Asymmetric [4+3] Annulation of C,N-Cyclic Azomethine Imines with Copper Allenylidenes
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ORGANIC LETTERS, 2018, 20 (20) : 6506 - 6510
[2] A [4+3] Cycloaddition Reaction of Aza-ortho-quinone Methides with C,N-Cyclic Azomethine Imines for Synthesis of 1,2,4-Triaze-pines
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[3] [4+3] Cycloaddition of in situ generated azoalkenes with C,N-cyclic azomethine imines: efficient synthesis of tetrazepine derivatives
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[4] Catalytic Asymmetric (4+3) Cyclizations of In Situ Generated ortho-Quinone Methides with 2-Indolylmethanols
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[5] Mechanisms of phosphine-catalyzed [4+3] annulation of allenoates with C, N-cyclic azomethine imines: A DFT investigation
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[6] Phosphine-Catalyzed [3+2] and [4+3]Annulation Reactions of C,N-Cyclic Azomethine Imines with Allenoates
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[7] Silver(I)- and Base-Mediated formal [4+3] Cycloaddition of in Situ generated 1,2-Diaza-1,3-dienes with C,N-Cyclic Azomethine Imines: An Efficient Protocol for the Synthesis of Tetrazepine Derivatives
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[8] Organocatalytic Diastereoselective Dearomative [4+2] Cyclodimerization of In-situ Generated ortho-Quinone Methides
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[10] Phosphine-Catalyzed Enantioselective [4+3] Annulation of Allenoates with C,N-Cyclic Azomethine Imines: Synthesis of Quinazoline-Based Tricyclic Heterocycles
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