New and regioselective synthesis of 4-ylidene-tetronic acids by Lewis-acid catalyzed cyclization of 4-alkoxy-bis-(trimethylsiloxy)-1,3-diene with oxalyl chloride

被引：0

作者：

Langer, P ^{[1
]}

Eckardt, T ^{[1
]}

机构：

[1] Univ Gottingen, Inst Organ Chem, D-37077 Gottingen, Germany

来源：

SYNLETT | 2000年 / 06期

关键词：

butenolides; cyclizations; dianion synthons; oxalic acid; regioselectivity;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new approach for the synthesis of 4-ylidene-tetronic acids is reported which involves Me3SiOTf-catalyzed, regio- and stereoselective cyclization of 4-alkoxy-bis-(trimethylsiloxy)-1,3-dienes with oxalyl chloride and subsequent chemoselective deprotection of the 3-hydroxy-group.

引用

页码：844 / 846

页数：3

共 13 条

[1] Regioselective synthesis of medium-sized bicyclic butenolides by Lewis acid catalyzed cyclization of cyclic 1,3-bis(trimethylsilyloxy)-1,3-butadienes with oxalyl chloride
Langer, P
Saleh, NNR
ORGANIC LETTERS, 2000, 2 (21) : 3333 - 3336
[2] The first 4-chloro-1,3-bis(trimethylsilyloxy)-1,3-diene and its application to the regioselective synthesis of chlorinated arenes
Reim, Stefanie
Langer, Peter
TETRAHEDRON LETTERS, 2008, 49 (14) : 2329 - 2332
[3] Regio- and diastereoselective synthesis of lissoclinolide analogues by Lewis acid catalyzed cyclization of the first 1,5-bis(trimethylsilyloxy)-1,3,5-hexatrienes with oxalyl chloride
Langer, P
Freifeld, I
SYNLETT, 2001, (04) : 523 - 525
[4] Synthesis of 4-alkoxycarbonyl-butenolides by uncatalyzed one-pot cyclization of 1,3-bis(silyloxy)alk-1-enes with oxalyl chloride
Dede, Ruediger
Michaelis, Lars
Fuentes, Dilver
Yawer, Mirza Arfan
Hussain, Lbrar
Fischer, Christine
Langer, Peter
TETRAHEDRON, 2007, 63 (51) : 12547 - 12561
[5] Synthesis of new 1,3-bis(Heteroaryl)-4,5-imidazolidinediones through reaction of N,N′-bis(Heteroaryl)methanediamines with oxalyl chloride
Ghandi, Mehdi
Salimi, Farshid
SYNTHETIC COMMUNICATIONS, 2007, 37 (4-6) : 637 - 644
[6] 4-tert-Butoxy-1-ethoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene. A New Diene and its Application to the Synthesis of γ-Alkylidenetetronic Acids
Van Thi Hong Nguyen
Bui Duy Cam
Ahmed, Zafar
Langer, Peter
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2013, 68 (07): : 836 - 840
[7] Lewis acid-induced intramolecular Friedel-Crafts cyclization of 1,3-bis-exocyclic dienes. A new route to 4a-methyltetrahydrofluorenes
Lomberget, T
Bentz, E
Bouyssi, D
Balme, G
ORGANIC LETTERS, 2003, 5 (12) : 2055 - 2057
[8] SYNTHESIS OF STERICALLY HINDERED BICYCLO[2.2.2]OCTANES BY LEWIS ACID-CATALYZED REACTION OF 2-(TRIMETHYLSILOXY)-1,3-CYCLOHEXADIENES WITH 4-METHYL-3-PENTEN-2-ONE
ASAOKA, M
ISHIBASHI, K
TAKAHASHI, W
TAKEI, H
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (06) : 2259 - 2260
[9] A NEW 1,3-OXATHIOLANE SYNTHESIS - SPIROCYCLIC 1,3-OXATHIOLANES FROM THE LEWIS-ACID-CATALYZED REACTION OF 1,3-THIAZOLE-5(4H)-THIONES AND OXIRANES
TROMM, PC
HEIMGARTNER, H
HELVETICA CHIMICA ACTA, 1990, 73 (08) : 2287 - 2294
[10] A new multicomponent reaction catalyzed by a [Lewis acid]+[Co(CO)4]- catalyst:: Stereospecific synthesis of 1,3-oxazinane-2,4-diones from epoxides, isocyanates, and CO
Church, Tamara L.
Byrne, Christopher M.
Lobkovsky, Emil B.
Coates, Geoffrey W.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (26) : 8156 - 8162

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