Organocatalytic Synthesis of Highly Substituted Furfuryl Alcohols and Amines

被引：60

作者：

Clark, J. Stephen ^{[1
]}

Boyer, Alistair ^{[1
]}

Aimon, Anthony ^{[1
]}

Garcia, Paloma Engel ^{[1
]}

Lindsay, David M. ^{[1
]}

Symington, Andrew D. F. ^{[1
]}

Danoy, Yves ^{[1
]}

机构：

[1] Univ Glasgow, Sch Chem, Glasgow G12 8QQ, Lanark, Scotland

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2012年 / 51卷 / 48期

基金：

英国工程与自然科学研究理事会;

关键词：

domino reactions; enynes; furans; organocatalysis; thioethers; CARBONYL-COMPOUNDS; FURANS; ROUTE; LOPHOTOXIN; ACID;

D O I：

10.1002/anie.201207300

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Top cat! Tetrahydrothiophene is an efficient organocatalyst for the synthesis of highly substituted furfuryl products from readily accessible electron-poor enynes under neutral reaction conditions. This process is applicable to a wide range of nucleophiles and enynes and can be used in a domino organocatalysis sequence. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：12128 / 12131

页数：4

共 53 条

[1] STRUCTURE ACTIVITY AND MOLECULAR MODELING STUDIES OF THE LOPHOTOXIN FAMILY OF IRREVERSIBLE NICOTINIC RECEPTOR ANTAGONISTS [J].

ABRAMSON, SN ;

TRISCHMAN, JA ;

TAPIOLAS, DM ;

HAROLD, EE ;

FENICAL, W ;

TAYLOR, P .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (06) :1798-1804

[2] SYNTHESIS OF METHYL 2,3-DIDEOXY-DL-ALK-2-ENOPYRANOSIDES FROM FURAN COMPOUNDS - GENERAL APPROACH TO TOTAL SYNTHESIS OF MONOSACCHARIDES [J].

ACHMATOWICZ, O ;

BUKOWSKI, P ;

SZECHNER, B ;

ZWIERZCHOWSKA, Z ;

ZAMOJSKI, A .

TETRAHEDRON, 1971, 27 (10) :1973-+

[3] Catalytic, asymmetric sulfur ylide-mediated epoxidation of carbonyl compounds: Scope, selectivity, and applications in synthesis [J].

Aggarwal, VK ;

Winn, CL .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :611-620

[4] Organocatalytic Domino Reactions [J].

Alba, Andrea-Nekane ;

Companyo, Xavier ;

Viciano, Monica ;

Rios, Ramon .

CURRENT ORGANIC CHEMISTRY, 2009, 13 (14) :1432-1474

[5] An Organocatalytic Approach to 2-Hydroxyalkyl- and 2-Aminoalkyl Furanes [J].

Albrecht, Lukasz ;

Ransborg, Lars Krogager ;

Gschwend, Bjorn ;

Jorgensen, Karl Anker .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (50) :17886-17893

[6] Cu(I)-catalyzed regioselective synthesis of polysubstituted furans from propargylic esters via postulated (2-furyl)carbene complexes [J].

Barluenga, Jose ;

Riesgo, Lorena ;

Vicente, Ruben ;

Lopez, Luis A. ;

Tomas, Miguel .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (41) :13528-+

[7] Recent advances in the Baylis-Hillman reaction and applications [J].

Basavaiah, D ;

Rao, AJ ;

Satyanarayana, T .

CHEMICAL REVIEWS, 2003, 103 (03) :811-891

[8] Synthesis of pyridin derivates from Dichlor ether and beta-amino croton acid esters. [J].

Benary, E .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1911, 44 :489-493

[9] Application of furyl-stabilized sulfur ylides to a concise synthesis of 8a-epi-swainsonine [J].

Bi, Jie ;

Aggarwal, Varinder K. .

CHEMICAL COMMUNICATIONS, 2008, (01) :120-122

[10]

Boto A, 2011, HETEROCYCLES IN NATURAL PRODUCT SYNTHESIS, P99

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