Iron(III) chloride-catalysed direct nucleophilic α-substitution of Morita-Baylis-Hillman alcohols with alcohols, arenes, 1,3-dicarbonyl compounds, and thiols

被引：40

作者：

Zhang, Xiaoxiang ^{[1
]}

Rao, Weidong ^{[1
]}

Chan, Sally Wai Hong ^{[1
]}

Chan, Philip Wai Hong ^{[1
]}

机构：

[1] Nanyang Technol Univ, Sch Math & Phys Sci, Div Chem & Biol Chem, Singapore 637371, Singapore

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 20期

关键词：

EFFICIENT STEREOSELECTIVE-SYNTHESIS; FRIEDEL-CRAFTS ALKYLATION; ONE-STEP SYNTHESIS; ALLYLIC ALCOHOLS; FACILE SYNTHESIS; PROPARGYLIC ALCOHOLS; BENZYLIC ALCOHOLS; DIRECT AMINATION; METAL CATALYSIS; TANDEM REACTION;

D O I：

10.1039/b908447a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general and efficient direct method for the alpha-substitution of Morita-Baylis-Hillman alcohols with carbon-and heteroatom-centred nucleophiles such as alcohols, arenes, 1,3-dicarbonyl compounds, and thiols in the presence of FeCl3 center dot 6H(2)O as catalyst has been developed. The reaction is operationally straightforward, accomplished in good to excellent product yields (40-99%) and with exclusive alpha-regioselectivity under mild conditions that did not need an inert and moisture-free environment.

引用

页码：4186 / 4193

页数：8

共 24 条

[21] Indium(III) Chloride-Catalyzed Propargylation/Amination/Cycloisomerization Tandem Reaction: One-Pot Synthesis of Highly Substituted Pyrroles from Propargylic Alcohols, 1,3-Dicarbonyl Compounds and Primary Amines
Liu, Xiao-tao
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ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (17) : 2778 - 2788
[22] Iron(III)-Catalyzed Four-Component Coupling Reaction of 1,3-Dicarbonyl Compounds, Amines, Aldehydes, and Nitroalkanes: A Simple and Direct Synthesis of Functionalized Pyrroles
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[23] Bronsted acid ionic liquid-catalyzed direct benzylation, allylation and propargylation of 1,3-dicarbonyl compounds with alcohols as well as one-pot synthesis of 4H-chromenes
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TETRAHEDRON, 2009, 65 (36) : 7457 - 7463
[24] STUDY OF MECHANISMS OF REACTIONS OF 1,3-DICARBONYL COMPOUNDS WITH NUCLEOPHILIC-REAGENTS .8. EFFECT OF SUBSTITUENTS IN NUCLEOPHILE AND SUBSTRATE ON KINETICS OF THE REACTION OF SUBSTITUTED BENZYL ALCOHOLS WITH 4-AROYL-5-METHOXYCARBOHYL-1-PHENYL-2,3-DIHYDROPYRROLE-2,3-DIONES
KOZLOV, AP
PEREVOZCHIKOV, LA
MASLIVETS, AN
ANDREICHIKOV, YS
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