ROMPgel-supported thiazolium iodide: An efficient supported organic catalyst for parallel stetter reactions

被引：43

作者：

Barrett, AGM ^{[1
]}

Love, AC ^{[1
]}

Tedeschi, L ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 19期

关键词：

D O I：

10.1021/ol048694u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A high-loading ROMPgel-supported thiazolium iodide was prepared via ROM Polymerization of the corresponding norbornene-derived monomer. The resulting ionic ROMPgel proved to be an efficient organic catalyst for Stetter reactions. The 1,4-dicarbonyl products, important intermediates in the synthesis of cyclopentenones and heterocycles, were obtained in high yields and excellent purities after minimal purification. The ROMPgel could be reused in up to four consecutive reaction cycles without significant loss of catalytic activity.

引用

页码：3377 / 3380

页数：4

共 33 条

[1] Synthesis and preliminary use of novel acrylic ester-derived task-specific ionic liquids [J].

Anjaiah, S ;

Chandrasekhar, S ;

Grée, R .

TETRAHEDRON LETTERS, 2004, 45 (03) :569-571

[2] Parallel synthesis of terminal alkynes using a ROMPgel-supported ethyl 1-diazo-2-oxopropylphosphonate [J].

Barrett, AGM ;

Hopkins, BT ;

Love, AC ;

Tedeschi, L .

ORGANIC LETTERS, 2004, 6 (05) :835-837

[3] ROMPgel reagents in parallel synthesis [J].

Barrett, AGM ;

Hopkins, BT ;

Köbberling, J .

CHEMICAL REVIEWS, 2002, 102 (10) :3301-3323

[4]

CASTELLS J, 1978, ISRAEL J CHEM, V17, P278

[5] POLYMER-ATTACHED THIAZOLIUM SALTS CATALYZED ADDITION OF ALDEHYDES TO ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS [J].

CHANG, BH ;

CHANG, YL .

JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1983, 30 (01) :55-58

[6] DERIVATIVES OF 5-HYDROXYMETHYL-FURFURAL .1. SYNTHESIS OF DIFURAN AND TERFURAN DERIVATIVES [J].

ELHAJJ, T ;

MARTIN, JC ;

DESCOTES, G .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (01) :233-235

[7] Nucleophilic carbenes in asymmetric organocatalysis [J].

Enders, D ;

Balensiefer, T .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :534-541

[8]

Flynn DL, 2002, CURR OPIN DRUG DI DE, V5, P571

[9] A short and efficient synthesis of (±)-trans-sabinene hydrate [J].

Galopin, CC .

TETRAHEDRON LETTERS, 2001, 42 (33) :5589-5591

[10] STETTER CONDENSATION CATALYZED BY A POLYMER-BOUND THIAZOLIUM YLIDE [J].

HO, TL ;

LIU, SH .

SYNTHETIC COMMUNICATIONS, 1983, 13 (13) :1125-1127

← 1 2 3 4 →