Design of resolving reagents: p-Substituted mandelic acids as resolving reagents for 1-arylalkylamines

被引:58
作者
Kinbara, K
Sakai, K
Hashimoto, Y
Nohira, H
Saigo, K
机构
[1] UNIV TOKYO,GRAD SCH ENGN,DEPT CHEM & BIOTECHNOL,BUNKYO KU,TOKYO 113,JAPAN
[2] SAITAMA UNIV,FAC ENGN,DEPT APPL CHEM,URAWA,SAITAMA 338,JAPAN
基金
日本学术振兴会;
关键词
CYCLIC PHOSPHORIC-ACIDS; OPTICAL RESOLUTION; AGENTS;
D O I
10.1016/0957-4166(96)00175-9
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The resolution of 1-arylakylamines 2-10 by mandelic acid 1 was studied. It was found that a substituent, which elongated the molecular length of the amines, diminished the resolution efficiency. On the basis of these results, (S)-p-methylmandelic acid (S)-11 and (R)-p-methoxymandelic acid (R)-12 were selected as new resolving reagents for the 1-arylalkylamines; these acids were found to have a higher resolving ability than (R)-1. (C) 1996 Elsevier Science Ltd
引用
收藏
页码:1539 / 1542
页数:4
相关论文
共 9 条
  • [1] GHARPURE MM, 1988, SYNTHESIS-STUTTGART, P410
  • [2] SEMISYNTHETIC CEPHALOSPORINS - SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF "7-MANDELAMIDO-3-CEPHEM-4-CARBOXYLIC ACIDS
    HOOVER, JRE
    DUNN, GL
    JAKAS, DR
    LAM, LL
    TAGGART, JJ
    GUARINI, JR
    PHILLIPS, L
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1974, 17 (01) : 34 - 41
  • [3] Jacques J., 1994, ENANTIOMERS RACEMATE
  • [4] NEWMAN P, 1981, OTICAL RESOLUTION PR, V1
  • [5] OPTICAL RESOLUTION OF 2-AMINO-1,2-DIPHENYLETHANOL BY PREFERENTIAL CRYSTALLIZATION AND ITS UTILIZATION IN FRACTIONAL CRYSTALLIZATION AND ENANTIOSELECTIVE REDUCTION OF PROCHIRAL KETONES
    SAIGO, K
    OGAWA, S
    KIKUCHI, S
    KASAHARA, A
    NOHIRA, H
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1982, 55 (05) : 1568 - 1573
  • [6] OPTICAL RESOLUTION OF 1-(3-METHOXYPHENYL)ETHYLAMINE WITH ENANTIOMERICALLY PURE MANDELIC-ACID, AND THE CRYSTAL-STRUCTURE OF LESS-SOLUBLE DIASTEREOMERIC SALT
    SAKAI, K
    HASHIMOTO, Y
    KINBARA, K
    SAIGO, K
    MURAKAMI, H
    NOHIRA, H
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1993, 66 (11) : 3414 - 3418
  • [7] THE CHIRAL AMINO ALCOHOL, CIS-2-AMINO-1-ACENAPHTHENOL - SYNTHESIS, RESOLUTION, AND APPLICATION TO THE DIASTEREOSELECTIVE [2,3]-WITTIG REARRANGEMENT
    SUDO, A
    HASHIMOTO, Y
    KIMOTO, H
    HAYASHI, K
    SAIGO, K
    [J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (07) : 1333 - 1346
  • [8] THE DESIGN OF RESOLVING AGENTS - CHIRAL CYCLIC PHOSPHORIC-ACIDS
    TENHOEVE, W
    WYNBERG, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (23) : 4508 - 4514
  • [9] VANDERHAEST AD, 1993, RECL TRAV CHIM PAY B, V112, P230