COMPLEX-INDUCED PROXIMITY EFFECTS IN ENOLATE FORMATION - HIGHLY DIASTEREOSELECTIVE ALPHA-METHYLATION OF BINAPHTHYL ESTERS OF ARYLACETIC ACIDS

被引:22
作者
FUJI, K [1 ]
NODE, M [1 ]
TANAKA, F [1 ]
机构
[1] KYOTO PHARMACEUT UNIV,YAMASHINA KU,KYOTO 607,JAPAN
关键词
D O I
10.1016/S0040-4039(00)97115-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Highly diastereoselective methylation of binaphthyl esters of arylacetic acids and its application to the syntheses of antiinflammatory drugs, (S)- suprofen and (S)-naproxen. © 1990.
引用
收藏
页码:6553 / 6556
页数:4
相关论文
共 12 条
[1]   STEREOCONTROL AND REGIOCONTROL BY COMPLEX INDUCED PROXIMITY EFFECTS - REACTIONS OF ORGANOLITHIUM COMPOUNDS [J].
BEAK, P ;
MEYERS, AI .
ACCOUNTS OF CHEMICAL RESEARCH, 1986, 19 (11) :356-363
[2]  
CAPETOLA RJ, 1980, J PHARMACOL EXP THER, V214, P16
[3]   BINAPHTHOL AS A CHIRAL AUXILIARY - ASYMMETRIC ALKYLATION OF ARYLACETIC ACID [J].
FUJI, K ;
NODE, M ;
TANAKA, F ;
HOSOI, S .
TETRAHEDRON LETTERS, 1989, 30 (21) :2825-2828
[4]   A STEREOCONVERGENT STRATEGY FOR THE SYNTHESIS OF ENANTIOMERICALLY PURE (R)-(-) AND (S)-(+)-2-(6-METHOXY-2-NAPHTHYL)-PROPANOIC ACID (NAPROXEN) [J].
GIORDANO, C ;
CASTALDI, G ;
CAVICCHIOLI, S ;
VILLA, M .
TETRAHEDRON, 1989, 45 (13) :4243-4252
[5]   NONSTEROIDAL ANTIINFLAMMATORY AGENTS .1. 6-SUBSTITUTED 2-NAPHTHYLACETIC ACIDS [J].
HARRISON, IT ;
LEWIS, B ;
NELSON, P ;
ROOKS, W ;
ROSZKOWS.A ;
TOMOLONI.A ;
FRIED, JH .
JOURNAL OF MEDICINAL CHEMISTRY, 1970, 13 (02) :203-&
[6]   ESTER ENOLATE CLAISEN REARRANGEMENT - STEREOCHEMICAL CONTROL THROUGH STEREOSELECTIVE ENOLATE FORMATION [J].
IRELAND, RE ;
MUELLER, RH ;
WILLARD, AK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (10) :2868-2877
[7]  
JANSSEN PAJ, 1975, ARZNEIMITTEL-FORSCH, V25, P1495
[8]  
PUJALTE J, 1984, CURR THER RES CLIN E, V36, P245
[9]   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
[10]   STRUCTURES OF 3 LITHIUM ESTER ENOLATES BY X-RAY-DIFFRACTION - DERIVATION OF REACTION-PATH FOR CLEAVAGE INTO KETENE AND ALCOHOLATE [J].
SEEBACH, D ;
AMSTUTZ, R ;
LAUBE, T ;
SCHWEIZER, WB ;
DUNITZ, JD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (19) :5403-5409