Highly enantioselective hydrogenation of α,β-unsaturated phosphonates with iridium-phosphinooxazoline complex:: synthesis of a phosphorus analogue of naproxen

被引：56

作者：

Goulioukina, NS

Dolgina, TM

Bondarenko, GN

Beletskaya, IP

Ilyin, MM

Davankov, VA

Pfaltz, A

机构：

[1] Moscow MV Lomonosov State Univ, Dept Chem, Moscow 119992, Russia

[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 117813, Russia

[3] Univ Basel, Dept Chem, CH-4056 Basel, Switzerland

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 10期

关键词：

D O I：

10.1016/S0957-4166(03)00224-6

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A number of pharmaceutically interesting optically active 1-arylethylphosphonates, including a phosphorus analogue of naproxen, has been synthesized with ee 92-95% via asymmetric hydrogenation under mild conditions using [Ir(cod)(phosphine oxazoline)](+) [BArF](-) catalysts. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：1397 / 1401

页数：5

共 19 条

[1] BELLUCCI C, 1989, FARMACO, V44, P1167
[2] The asymmetric synthesis of alpha-substituted alpha-methyl and alpha-phenyl phosphonic acids: Design, carbanion geometry, reactivity and preparative aspects of chiral alkyl bicyclic phosphonamides
Bennani, YL
Hanessian, S
[J]. TETRAHEDRON, 1996, 52 (44) : 13837 - 13866
[3] Photo-Arbuzov rearrangements of benzylic phosphites. Stereochemistry at migratory carbon
Bhanthumnavin, W
Arif, A
Bentrude, WG
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (22) : 7753 - 7758
[4] BONDARENKO NA, IN PRESS KHIM PHARM
[5] PHOTOREARRANGEMENTS OF BENZYL PHOSPHITES - STEREOCHEMISTRY AT PHOSPHORUS
CAIRNS, SM
BENTRUDE, WG
[J]. TETRAHEDRON LETTERS, 1989, 30 (09) : 1025 - 1028
[6] 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
[7] 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
[8] A practical synthetic approach to chiral α-aryl substituted ethylphosphonates
Goulioukina, NS
Dolgina, TM
Beletskaya, IP
Henry, JC
Lavergne, D
Ratovelomanana-Vidal, V
Genet, JP
[J]. TETRAHEDRON-ASYMMETRY, 2001, 12 (02) : 319 - 327
[9] GOULIOUKINA NS, IN PRESS ZH ORG KHIM
[10] GOULIOUKINA NS, 2002, ZH ORG KHIM, V38, P600

← 1 2 →