DABCO-catalyzed reaction of allenic esters and ketones with salicyl N-tosylimines:: Synthesis of highly functionalized chromenes

被引：148

作者：

Shi, YL ^{[1
]}

Shi, M ^{[1
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 14期

关键词：

D O I：

10.1021/ol051044l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

DABCO-catalyzed reactions of salicyl N-tosylimines with ethyl 2,3-butadienoate and penta-3,4-dien-2-one proceed smoothly at room temperature in dichloromethane to give the corresponding chromenes in good to excellent yields.

引用

页码：3057 / 3060

页数：4

共 24 条

[1] Reevaluation of the mechanism of the Baylis-Hillman reaction: Implications for asymmetric catalysis [J].

Aggarwal, VK ;

Fulford, SY ;

Lloyd-Jones, GC .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (11) :1706-1708

[2] DISCOVERY OF INSECT ANTI-JUVENILE HORMONES IN PLANTS [J].

BOWERS, WS ;

OHTA, T ;

CLEERE, JS ;

MARSELLA, PA .

SCIENCE, 1976, 193 (4253) :542-547

[3] Novel heteroarotinoids as potential antagonists of Mycobacterium bovis BCG [J].

Brown, CW ;

Liu, SQ ;

Klucik, J ;

Berlin, KD ;

Brennan, PJ ;

Kaur, D ;

Benbrook, DM .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (04) :1008-1017

[4]

Couladouros EA, 2002, ANGEW CHEM INT EDIT, V41, P3677, DOI 10.1002/1521-3773(20021004)41:19<3677::AID-ANIE3677>3.0.CO

[5]

2-Y

[6]

Ellis G.P., 1977, Chromenes, chromanones, and chromones, DOI 10.1002/9780470187012

[7] Amine-catalyzed coupling of allenic esters to α,β-unsaturated carbonyls [J].

Evans, CA ;

Miller, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (41) :12394-12395

[8] Asymmetric catalysis with "planar-chiral" derivatives of 4-(dimethylamino)pyridine [J].

Fu, GC .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :542-547

[9] Does the DABCO-catalysed reaction of 2-hydroxybenzaldehydes with methyl acrylate follow a Baylis-Hillman pathway? [J].

Kaye, PT ;

Musa, MA ;

Nocanda, XW ;

Robinson, RS .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (07) :1133-1138

[10] Discovery of 4-aryl-4H-chromenes as a new series of apoptosis inducers using a cell- and caspase-based high-throughput screening assay.: 1.: Structure-activity relationships of the 4-aryl group [J].

Kemnitzer, W ;

Drewe, J ;

Jiang, SC ;

Zhang, H ;

Wang, Y ;

Zhao, JH ;

Jia, SJ ;

Herich, J ;

Labreque, D ;

Storer, R ;

Meerovitch, K ;

Bouffard, D ;

Rej, R ;

Denis, R ;

Blais, C ;

Lamothe, S ;

Attardo, G ;

Gourdeau, H ;

Tseng, B ;

Kasibhatla, S ;

Cai, SX .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (25) :6299-6310

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