Mild and Rapid Method for the Generation of ortho-(Naphtho)quinone Methide Intermediates

被引：48

作者：

Shaikh, Abdul Kadar ^{[1
]}

Cobb, Alexander J. A. ^{[2
]}

Varvounis, George ^{[1
]}

机构：

[1] Univ Ioannina, Dept Chem, Sect Organ Chem & Biochem, GR-45110 Ioannina, Greece

[2] Univ Reading, Sch Pharm, Reading RG6 6AD, Berks, England

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 02期

关键词：

O-QUINONE METHIDES; DIELS-ALDER REACTIONS; AQUEOUS-SOLUTION; BIOMIMETIC SYNTHESIS; EFFICIENT METHOD; CROSS-LINKING; DERIVATIVES; TAUTOMERIZATION; PHOTOGENERATION; (+/-)-ALBOATRIN;

D O I：

10.1021/ol203196n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new mild method has been devised for generating o-(naphtho)quinone methides via fluoride-induced desilylation of silyl derivatives of o-hydroxybenzyl(or 1-naphthylmethyl) nitrate. The reactive o-(naphtho)quinone methide intermediates were trapped by C, O, N, and S nucleophiles and underwent "inverse electron-demand" hetero-Diels-Alder reaction with dienophiles to give stable adducts. The method has useful potential application in natural product synthesis and drug research.

引用

页码：584 / 587

页数：4

共 6 条

[1] Applications of ortho-Quinone Methide Intermediates in Catalysis and Asymmetric Synthesis
Pathak, Tejas P.
Sigman, Matthew S.
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (22) : 9210 - 9215
[2] Novel Synthesis of 3-Substituted 2,3-Dihydrobenzofurans via ortho-Quinone Methide Intermediates Generated in Situ
Shaikh, Abdul Kadar
Varvounis, George
ORGANIC LETTERS, 2014, 16 (05) : 1478 - 1481
[3] Aza-Ortho-Quinone Methides as Reactive Intermediates: Generation and Utility in Contemporary Asymmetric Synthesis
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[4] Traceless piperidine-assisted one-pot tandem dearomative spiroannulation of phenolic compounds with nitrile oxides via ortho-quinone methide intermediates
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[5] Traceless piperidine-assisted one-pot tandem dearomative spiroannulation of phenolic compounds with nitrile oxides via ortho-quinone methide intermediates
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Liu, Yan
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ARKIVOC, 2024,
[6] Generation and Conjugate Additions of o-Quinone Methides Under Mild Base Conditions: Rapid Synthesis of N-Substituted Aryl Glycine Derivatives
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Wang, Xiangmin
Chen, Jinchun
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (36) : 8299 - 8306

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