Preparation of halo enol phostones by reaction of acetylenic phosphonate monoesters with (bis-collidine)halo hexafluorophosphate

被引：11

作者：

Andre, Virginie ^{[1
]}

Robin, Sylvie ^{[1
]}

Rousseau, Gerard ^{[1
]}

机构：

[1] Univ Paris 11, ICMMO, Lab Synth Organ & Methodol, F-91405 Orsay, France

来源：

TETRAHEDRON LETTERS | 2008年 / 49卷 / 34期

关键词：

electrophilic cyclization; bromo reagent; iodo reagent; phosphorus compound; heterocyclic compound; phospho lactone; enol;

D O I：

10.1016/j.tetlet.2008.06.037

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of non-conjugated acetylenic phosphonate monoesters with (bis-collidine) bromo and iodo hexafluorophosphates was found to lead to the formation of halo enol phostones. Depending on the size of the heterocyclic compounds formed (6-8-membered compounds), endo or a mixture of endo and exo cyclization products were obtained. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：5059 / 5062

页数：4

共 23 条

[1] Reaction of unsaturated phosphonate monoesters with bromo- and iodo(bis-collidine) hexafluorophosphates [J].

Andre, Virginie ;

Lahrache, Hind ;

Robin, Sylvie ;

Rousseau, Gerard .

TETRAHEDRON, 2007, 63 (40) :10059-10066

[2]

CHAKRAVARTY PK, 1982, J BIOL CHEM, V257, P610

[3]

DOI JT, 1989, J ORG CHEM, V54, P2764, DOI 10.1021/jo00272a061

[4] Remarkable electronic and steric effects in the nitrile biotransformations for the preparation of enantiopure functionalized carboxylic acids and amides: Implication for an unsaturated carbon-carbon bond binding domain of the amidase [J].

Gao, Ming ;

Wang, De-Xian ;

Zheng, Qi-Yu ;

Huang, Zhi-Tang ;

Wang, Mei-Xiang .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (16) :6060-6066

[5]

GowriSankar S, 2004, B KOREAN CHEM SOC, V25, P1963

[6] SYNTHESIS OF HALO ENOL LACTONES - MECHANISM-BASED INACTIVATORS OF SERINE PROTEASES [J].

KRAFFT, GA ;

KATZENELLENBOGEN, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) :5459-5466

[7] Halodephosphorylation of α,β-unsaturated phosphonic acid monoesters [J].

Lahrache, H ;

Robin, S ;

Rousseau, G .

TETRAHEDRON LETTERS, 2005, 46 (10) :1635-1637

[8] Structural and functional consequences of haloenol lactone inactivation of murine and human glutathione S-transferase [J].

Mitchell, AE ;

Zheng, J ;

Hammock, BD ;

Lo Bello, M ;

Jones, AD .

BIOCHEMISTRY, 1998, 37 (19) :6752-6759

[9] Haloenol lactones as inactivators and substrates of aldehyde dehydrogenase [J].

Mukerjee, N ;

Dryjanski, M ;

Dai, W ;

Katzenellenbogen, JA ;

Pietruszko, R .

JOURNAL OF PROTEIN CHEMISTRY, 1996, 15 (07) :639-648

[10] Bruchins-mitogenic 3-(hydroxypropanoyl) esters of long chain diols from weevils of the bruchidae [J].

Oliver, JE ;

Doss, RP ;

Williamson, RT ;

Carney, JR ;

DeVilbiss, ED .

TETRAHEDRON, 2000, 56 (39) :7633-7641

← 1 2 3 →