Lewis Base-Catalyzed [4+3] Annulation of ortho-Quinone Methides and MBH Carbonates: Synthesis of Functionalized Benzo[b]oxepines Bearing Oxindole Scaffolds

被引：59

作者：

Du, Ji-Yuan ^{[1
]}

Ma, Yan-Hua ^{[1
]}

Meng, Fan-Xiao ^{[1
]}

Zhang, Rui-Rui ^{[1
]}

Wang, Ruo-Nan ^{[1
]}

Shi, Hong-Liang ^{[1
]}

Wang, Qi ^{[1
]}

Fan, Ya-Xin ^{[1
]}

Huang, Hong-Li ^{[1
]}

Cui, Ji-Chun ^{[1
]}

Ma, Chun-Lin ^{[1
]}

机构：

[1] Liaocheng Univ, Coll Chem & Chem Engn, Liaocheng 252059, Shandong, Peoples R China

来源：

ORGANIC LETTERS | 2019年 / 21卷 / 02期

关键词：

BAYLIS-HILLMAN CARBONATES; ONE-POT SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; CYCLOADDITION REACTION; ASYMMETRIC-SYNTHESIS; O-QUINODIMETHANES; ALLENIC ESTERS; DERIVATIVES; ISATINS; ACCESS;

D O I：

10.1021/acs.orglett.8b03709

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel Lewis base-catalyzed [4 + 3] annulation process for the construction of benzo[b]oxepine scaffolds has been developed. 1,4-Diazabicyclo[2.2.2]octane (DABCO) promotes the union of o-QMs and Morita-Baylis-Hillman carbonates in reasonable to excellent yields and good stereoselectivities (dr > 20:1). This straightforward, catalytic approach offers access to a variety of synthetically useful benzo[b]oxepine derivatives bearing oxindole scaffolds containing all-carbon spiro-quaternary stereocenters.

引用

页码：465 / 468

页数：4

共 28 条

[1] A new cycloaddition profile for ortho-quinone methides: photoredox-catalyzed [6+4] cycloadditions for synthesis of benzo[b]cyclopenta[e]oxepines
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[2] Insights into Lewis base-catalyzed chemoselective [3+2] and [3+4] annulation reactions of MBH carbonates
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[4] Formal [4+2] Annulation of Oxindole-Embedded ortho-Quinone Methides with 1,3-Dicarbonyls: Synthesis of Spiro[Chromen-4,3'-Oxindole] Scaffolds
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[5] Base-mediated diastereoselective [4+3] annulation of in situ generated ortho-quinone methides with C, N-cyclic azomethine imines
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[6] Facile Synthesis of Spirocyclic Oxindole Scaffolds via Intermolecular [4+1] Cycloaddition of ortho-Quinone Methides with 3-Chlorooxindoles
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[7] Cinchona Alkaloid Catalyzed Enantioselective [4+2] Annulation of Allenic Esters and in Situ Generated ortho-Quinone Methides: Asymmetric Synthesis of Functionalized Chromans
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[8] N-Heterocyclic Carbene Catalyzed [4+3] Annulation of Enals and o-Quinone Methides: Highly Enantioselective Synthesis of Benzo-ε-Lactones
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[9] Lewis Acid-Catalyzed Unusual (4+3) Annulation of para-Quinone Methides with Bicyclobutanes: Access to Oxabicyclo[4.1.1]Octanes
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[10] Transition-Metal-Free [4+3]-Cycloaddition of ortho-Quinone Methides and Isomunchnones: Catalytic and Diastereoselective Assembly of Oxa-bridged Oxazocine Scaffolds
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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (49) : 16185 - 16189

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