Dioxirane oxidation of substituted vinylphosphonates: a novel efficient route to 1,2-epoxyalkylphosphonates

被引：23

作者：

Cristau, HJ ^{[1
]}

Mbianda, XY ^{[1
]}

Geze, A ^{[1
]}

Beziat, Y ^{[1
]}

Gasc, MB ^{[1
]}

机构：

[1] ENSCM, Chim Organ Lab, CNRS,Unite Rech Associee, ESA 5076, F-34296 Montpellier 5, France

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 1998年 / 571卷 / 02期

关键词：

dioxirane; 1,2-epoxyphosphonate; vinylphosphonate; epoxidation; oxidation;

D O I：

10.1016/S0022-328X(98)00856-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A new stereoselective route to substituted 1,2-epoxyalkylphosphonates through oxidation of corresponding alk-1-enylphosphonates by 'in situ' generated ethylmethyldioxirane is described. (C) 1998 Elsevier Science S.A. All rights reserved.

引用

页码：189 / 193

页数：5

共 34 条

[1] DIOXIRANE EPOXIDATION OF ALPHA,BETA-UNSATURATED KETONES [J].

ADAM, W ;

HADJIARAPOGLOU, L ;

SMERZ, A .

CHEMISCHE BERICHTE, 1991, 124 (01) :227-232

[2] DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS [J].

ADAM, W ;

CURCI, R ;

EDWARDS, JO .

ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) :205-211

[3]

ADAM W, 1993, TOP CURR CHEM, V164, P46

[4] SILICON-DIRECTED ASYMMETRIC-SYNTHESIS OF (IR, 2S)-(-)-(1,2-EPOXYPROPYL)PHOSPHONIC ACID (FOSFOMYCIN) FROM (S)-LACTALDEHYDE [J].

BANDINI, E ;

MARTELLI, G ;

SPUNTA, G ;

PANUNZIO, M .

TETRAHEDRON-ASYMMETRY, 1995, 6 (09) :2127-2130

[5]

BECK HN, Patent No. 4692355

[6] PHOSPHONOMYCIN - STRUCTURE AND SYNTHESIS [J].

CHRISTENSEN, BG ;

LEANZA, WJ ;

BEATTIE, TR ;

PATCHETT, AA ;

ARISON, BH ;

ORMOND, RE ;

KUEHL, FA ;

ALBERSSC.G ;

JARDETZKY, O .

SCIENCE, 1969, 166 (3901) :123-+

[7]

CHRISTENSEN BG, 1969, Patent No. 1924135

[8]

COURREGELONGUE J, Patent No. 2596393

[9]

COUTROT P, 1978, SYNTHESIS-STUTTGART, P34

[10] A CONVENIENT STEREOSELECTIVE SYNTHESIS OF DISUBSTITUTED ALK-1-ENYL PHOSPHONATES [J].

CRISTAU, HJ ;

GASC, MB ;

MBIANDA, XY .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 474 (1-2) :C14-C15

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