PaaSicats:: Powerful catalysts for asymmetric epoxidation of enones.: Novel syntheses of α-arylpropanoic acids including (S)-fenoprofen

被引：44

作者：

Carde, L

Davies, H

Geller, TP

Roberts, SM

机构：

[1] Univ Liverpool, Dept Chem, Liverpool L69 7ZD, Merseyside, England

[2] Zeneca Pharmaceut, Macclesfield SK10 4TG, Cheshire, England

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 29期

关键词：

aluminium and compounds; asymmetric reactions; epoxidation; pharmacologically active compounds;

D O I：

10.1016/S0040-4039(99)01022-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Application of the recently developed silica-adsorbed polyleucine catalysts to the enantioselective epoxidation of Two enones is reported. Treatment of these epoxides with trimethylaluminium in moist dichloromethane generates the alpha-hydroxy-beta-methylketones, with inversion of configuration. Diastereoselective reduction of the ketone moiety followed by oxidative cleavage generates alpha-arylpropanoic acids. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：5421 / 5424

页数：4

共 21 条

[1] Improved procedure for Julia-Colonna asymmetric epoxidation of α,β-unsaturated ketones:: total synthesis of diltiazem and Taxol™ side-chain
Adger, BM
Barkley, JV
Bergeron, S
Cappi, MW
Flowerdew, BE
Jackson, MP
McCague, R
Nugent, TC
Roberts, SM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (23): : 3501 - 3507
[2] ALLEN JV, 1998, ADV BIOCH ENG BIOTEC, V63, P125
[3] ASYMMETRIC EPOXIDATION OF ELECTRON-POOR OLEFINS .5. INFLUENCE ON STEREOSELECTIVITY OF THE STRUCTURE OF POLY-ALPHA-AMINOACIDS USED AS CATALYSTS
BANFI, S
COLONNA, S
MOLINARI, H
JULIA, S
GUIXER, J
[J]. TETRAHEDRON, 1984, 40 (24) : 5207 - 5211
[4] Enzymatic resolution of (RS)-2-arylpropionic acid thioesters by Candida rugosa lipase-catalyzed thiotransesterification or hydrolysis in organic solvents
Chang, CS
Tsai, SW
Lin, CN
[J]. TETRAHEDRON-ASYMMETRY, 1998, 9 (16) : 2799 - 2807
[5] Catalytic asymmetric carbon-carbon bond forming reactions: preparation of optically enriched 2-aryl propionic acids by a catalytic asymmetric hydroboration-homologation sequence
Chen, AC
Ren, L
Crudden, CM
[J]. CHEMICAL COMMUNICATIONS, 1999, (07) : 611 - 612
[6] Lipase-catalyzed enantioselective esterification of ibuprofen in organic solvents under controlled water activity
Ducret, A
Trani, M
Lortie, R
[J]. ENZYME AND MICROBIAL TECHNOLOGY, 1998, 22 (04) : 212 - 216
[7] Synthetic applications of polymeric alpha-amino acids
Ebrahim, S
Wills, M
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (19) : 3163 - 3173
[8] ASYMMETRIC-SYNTHESIS OF ALPHA-METHYL CARBOXYLIC-ACID DERIVATIVES - STEREOCHEMISTRY IN ACIDIC RING-OPENING OF EPOXIDES
FUKUMASA, M
FURUHASHI, K
UMEZAWA, J
TAKAHASHI, O
HIRAI, T
[J]. TETRAHEDRON LETTERS, 1991, 32 (08) : 1059 - 1062
[9] GELLER TP, 1999, IN PRESS J CHEM S P1
[10] THE IMPORTANCE OF STEREOCHEMISTRY IN THE CLINICAL PHARMACOKINETICS OF THE 2-ARYLPROPIONIC ACID NON-STEROIDAL ANTI-INFLAMMATORY DRUGS
HUTT, AJ
CALDWELL, J
[J]. CLINICAL PHARMACOKINETICS, 1984, 9 (04) : 371 - 373

← 1 2 3 →