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.
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收藏
页码：5421 / 5424
页数：4
相关论文
共 21 条
[1]   Improved procedure for Julia-Colonna asymmetric epoxidation of α,β-unsaturated ketones:: total synthesis of diltiazem and Taxol™ side-chain [J].
Adger, BM ;
Barkley, JV ;
Bergeron, S ;
Cappi, MW ;
Flowerdew, BE ;
Jackson, MP ;
McCague, R ;
Nugent, TC ;
Roberts, SM .
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 [J].
BANFI, S ;
COLONNA, S ;
MOLINARI, H ;
JULIA, S ;
GUIXER, 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 [J].
Chang, CS ;
Tsai, SW ;
Lin, CN .
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 [J].
Chen, AC ;
Ren, L ;
Crudden, CM .
CHEMICAL COMMUNICATIONS, 1999, (07) :611-612
[6]   Lipase-catalyzed enantioselective esterification of ibuprofen in organic solvents under controlled water activity [J].
Ducret, A ;
Trani, M ;
Lortie, R .
ENZYME AND MICROBIAL TECHNOLOGY, 1998, 22 (04) :212-216
[7]   Synthetic applications of polymeric alpha-amino acids [J].
Ebrahim, S ;
Wills, M .
TETRAHEDRON-ASYMMETRY, 1997, 8 (19) :3163-3173
[8]   ASYMMETRIC-SYNTHESIS OF ALPHA-METHYL CARBOXYLIC-ACID DERIVATIVES - STEREOCHEMISTRY IN ACIDIC RING-OPENING OF EPOXIDES [J].
FUKUMASA, M ;
FURUHASHI, K ;
UMEZAWA, J ;
TAKAHASHI, O ;
HIRAI, T .
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 [J].
HUTT, AJ ;
CALDWELL, J .
CLINICAL PHARMACOKINETICS, 1984, 9 (04) :371-373
123