A practical synthetic approach to chiral α-aryl substituted ethylphosphonates

被引：78

作者：

Goulioukina, NS

Dolgina, TM

Beletskaya, IP

Henry, JC

Lavergne, D

Ratovelomanana-Vidal, V

Genet, JP

机构：

[1] Moscow State Univ, Dept Chem, Moscow 119899, Russia

[2] Ecole Natl Super Chim, UMR CNRS 7573, Lab Synth Select Organ & Prod Nat, F-75231 Paris 05, France

来源：

TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 02期

基金：

俄罗斯基础研究基金会;

关键词：

D O I：

10.1016/S0957-4166(01)00031-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A convenient general method is reported for the synthesis of alpha -aryl substituted ethylphosphonic acids and esters by hydrogenation of alpha -aryl substituted ethenylphosphonic acids and esters. Racemic alpha -arylethylphosphonic acids and esters were prepared in 70-88%, yield under palladium-assisted transfer hydrogenation conditions using ammonium formate. Asymmetric hydrogenation of alpha -arylethenylphosphonic acids using chiral Ru(II) catalysts led to alpha -arylethylphosphonic acids with enantiomeric excesses up to 86%. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：319 / 327

页数：9

共 61 条

[11] EXPLORATION OF PHENYL-SPACED 2-AMINO-(5-9)-PHOSPHONOALKANOIC ACIDS AS COMPETITIVE N-METHYL-D-ASPARTIC ACID ANTAGONISTS
BIGGE, CF
DRUMMOND, JT
JOHNSON, G
MALONE, T
PROBERT, AW
MARCOUX, FW
COUGHENOUR, LL
BRAHCE, LJ
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (07) : 1580 - 1590
[12] PREPARATION OF ORGANIC PHOSPHORUS COMPOUNDS BY IVANOV REACTIONS .2.
BLICKE, FF
RAINES, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1964, 29 (07) : 2036 - &
[13] PALLADIUM-CATALYZED HYDROGENATION OF ALPHA,BETA-UNSATURATED SULFONES AND PHOSPHONATES
CHO, IS
ALPER, H
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) : 4027 - 4028
[14] SELECTIVE REDUCTION OF MONOSUBSTITUTED AND DISUBSTITUTED OLEFINS BY SODIUM-BOROHYDRIDE AND COBALT(II)
CHUNG, SK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (06) : 1014 - 1016
[15] Addition reactions of the phosphorus halides V The formation of an unsaturated phosphonic acid
Conant, JB
Coyne, BB
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1922, 44 : 2530 - 2536
[16] Catalytically distinct antibodies prepared by the reactive immunization versus transition state analogue hapten manifolds
Datta, A
Wentworth, P
Shaw, JP
Simeonov, A
Janda, KD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (45) : 10461 - 10467
[17] STEREOSELECTIVE ALKYLATIONS OF CHIRAL, PHOSPHORUS-STABILIZED BENZYLIC CARBANIONS
DENMARK, SE
DOROW, RL
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (24) : 5926 - 5928
[18] ALKYLATIONS OF CHIRAL, PHOSPHORYL-STABILIZED AND THIOPHOSPHORYL-STABILIZED CARBANIONS
DENMARK, SE
CHEN, CT
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (48) : 11879 - 11897
[19] CYCLIC ORGANOPHOSPHORUS COMPOUNDS .8. CONFORMATION IN 1,3,2-DIOXAPHOSPH(V)ORINAN SERIES . PROTON MAGNETIC RESONANCE ASSIGNMENTS TO GEM-5,5-DIMETHYL GROUPS AND CONFORMATION AT PHOSPHORUS
EDMUNDSON, RS
MITCHELL, EW
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1968, (16): : 2091 - +
[20] PHOSPHONATES AS ANALOGS OF NATURAL PHOSPHATES
ENGEL, R
[J]. CHEMICAL REVIEWS, 1977, 77 (03) : 349 - 367

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