PREPARATION OF HOMOCHIRAL CROWN-ETHER CONTAINING (S)-1-(1-ADAMANTYL)ETHANE-1,2-DIOL AS A CHIRAL SUBUNIT AND ITS ENANTIOSELECTIVE COMPLEXATION WITH AN ORGANIC AMMONIUM CATION

被引：17

作者：

NAEMURA, K ^{[1
]}

MIZOOKU, T ^{[1
]}

KAMADA, K ^{[1
]}

HIROSE, K ^{[1
]}

TOBE, Y ^{[1
]}

SAWADA, M ^{[1
]}

TAKAI, Y ^{[1
]}

机构：

[1] OSAKA UNIV,INST SCI & IND RES,IBARAKI,OSAKA 567,JAPAN

来源：

TETRAHEDRON-ASYMMETRY | 1994年 / 5卷 / 08期

关键词：

D O I：

10.1016/0957-4166(94)80125-8

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Homochiral 1-(1-adamantyl)ethane-1,2-diol(5) was prepared and its absolute configuration was determined to be (S)-(+)-5 by enzymatic and H-1 n.m.r. spectroscopic methods. Using (S)-(+)-5 as a chiral subunit, the homochiral crown ether (+)-18 was synthesized and its enantioselectivity in complexation of methionine methyl ester perchlorate was also examined by the H-1 n.m.r. spectroscopic method.

引用

页码：1549 / 1558

页数：10

共 7 条

[1] PREPARATION AND ENANTIOMER RECOGNITION BEHAVIOR OF CROWN-ETHERS CONTAINING CIS-1-PHENYLCYCLOHEXANE-1,2-DIOL AND TRANS-1,2-DIPHENYLCYCLOHEXANE-1,2-DIOL AS A CHIRAL SUBUNIT
NAEMURA, K
MIYABE, H
SHINGAI, Y
TOBE, Y
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (09): : 1073 - 1077
[2] Preparation of homochiral phenolic crown ethers containing para-substituted phenol moiety and chiral subunits derived from (S)-1-phenylethane-1,2-diol: Their chiral recognition behaviour in complexation with neutral amines
Naemura, K
Nishikawa, Y
Fuji, J
Hirose, K
Tobe, Y
TETRAHEDRON-ASYMMETRY, 1997, 8 (06) : 873 - 882
[3] Preparation of homochiral azophenolic crown ethers containing 1-phenyltethane-1,2-diol and 2,4-dimethyl-3-oxapentane-1,5-diol as a chiral subunit: Enantiomer recognition behaviour towards chiral 2-aminoethanol derivatives
Naemura, K
Ogasahara, K
Hirose, K
Tobe, Y
TETRAHEDRON-ASYMMETRY, 1997, 8 (01) : 19 - 22
[4] Preparation and enantiomer recognition behaviour of azophenolic crown ethers containing cis-1-phenylcyclohexane-1,2-diol as the chiral subunit and 2,4-dinitrophenylazophenol as the chromophore
Naemura, K
Ueno, K
Takeuchi, S
Hirose, K
Tobe, Y
Kaneda, T
Sakata, Y
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (04): : 383 - 388
[5] Preparation of optically active azophenolic crown ethers containing 1-phenylethane-1,2-diol and 2,4-dimethyl-3-oxapentane-1,5-diol as a chiral subunit: temperature-dependent enantiomer selectivity in the complexation with chiral amines
Ogasahara, K
Hirose, K
Tobe, Y
Naemura, K
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (21): : 3227 - 3236
[6] Preparation of homochiral phenolic crown ether having chiral subunits derived from (1R,2S)-cis-1,2,3,4-tetrahydronaphthalene-1,2-diol: temperature-dependent enantioselectivity in complexations with neutral amines
Naemura, K
Wakebe, T
Hirose, K
Tobe, Y
TETRAHEDRON-ASYMMETRY, 1997, 8 (15) : 2585 - 2595
[7] Preparation of homochiral phenolic crown ether having chiral subunits derived from (1R,2S)-cis-1,2,3,4-tetrahydronaphthalene-1,2$MI N@diol: temperature-dependent enantioselectivity in complexations with neutral amines
Tetrahedron Asymmetry, 15 (2585):

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