NOVEL CATALYTIC ENANTIOSELECTIVE PROTONATION (PROTON-TRANSFER) IN MICHAEL ADDITION OF BENZENETHIOL TO ALPHA-ACRYLACRYLATES - SYNTHESIS OF (S)-NAPROXEN AND ALPHA-ARYLPROPIONIC ACIDS OR ESTERS

被引：108

作者：

KUMAR, A

SALUNKHE, RV

RANE, RA

DIKE, SY

机构：

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1991年 / 07期

关键词：

D O I：

10.1039/c39910000485

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel synthesis of optically active 2-phenylpropionic acids or esters via catalytic enantioselective protonation in the Michael addition of benzenethiol to 2-phenylacrylates is described; the synthetic utility is further demonstrated by the asymmetric synthesis of (S)-Naproxen.

引用

收藏

页码：485 / 486

页数：2

相关论文

共 11 条

[1]

CAMPOLMI S, 1979, Patent No. 2919919

[2]

CASTALDI G, 1987, J ORG CHEM, V52, P4243

[3]

DIJEKSTRA GDH, 1989, RECL TRAV CHIM PAY B, V108, P195

[4] CONFORMATIONAL STUDY OF CINCHONA ALKALOIDS - A COMBINED NMR, MOLECULAR MECHANICS, AND X-RAY APPROACH [J].

DIJKSTRA, GDH ;

KELLOGG, RM ;

WYNBERG, H ;

SVENDSEN, JS ;

MARKO, I ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (21) :8069-8076

[5] SYNTHESIS OF (R)-(+)-ALPHA-DAMASCONE AND (S)-(-)-ALPHA-DAMASCONE BY TANDEM GRIGNARD REACTION-ENANTIOSELECTIVE PROTONATION - EVIDENCE FOR THE INTERMEDIACY OF A CHIRAL COMPLEX [J].

FEHR, C ;

GALINDO, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (20) :6909-6911

[6] POLY(CINCHONA ALKALOID-CO-ACRYLONITRILE)S - NEW POLYMER CATALYSTS FOR ASYMMETRIC SYNTHESIS [J].

KOBAYASHI, N ;

IWAI, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (22) :7071-7072

[7] ASYMMETRIC ADDITION OF THIOGLYCOLIC ACID TO NITRO OLEFINS CATALYZED BY CINCHONA ALKALOIDS [J].

KOBAYASHI, N ;

IWAI, K .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (09) :1823-1828

[8] ALPHA-HYDROXY ESTERS AS CHIRAL REAGENTS - ASYMMETRIC-SYNTHESIS OF 2-ARYLPROPIONIC ACIDS [J].

LARSEN, RD ;

CORLEY, EG ;

DAVIS, P ;

REIDER, PJ ;

GRABOWSKI, EJJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (19) :7650-7651

[9]

NOYORI R, 1987, J ORG CHEM, V52, P3174

[10] METHODS FOR THE SYNTHESIS OF ANTIINFLAMMATORY 2-ARYL PROPIONIC ACIDS [J].

RIEU, JP ;

BOUCHERLE, A ;

COUSSE, H ;

MOUZIN, G .

TETRAHEDRON, 1986, 42 (15) :4095-4131