ASYMMETRIC OXYSELENENYLATION OF OLEFINS USING OPTICALLY-ACTIVE SELENOBINAPHTHYLS AND D-MENTHOL AS A NUCLEOPHILE

被引：34

作者：

FUJITA, K ^{[1
]}

IWAOKA, M ^{[1
]}

TOMODA, S ^{[1
]}

机构：

[1] UNIV TOKYO, COLL ARTS & SCI, DEPT CHEM, KOMABA, MEGURO KU, TOKYO 153, JAPAN

来源：

CHEMISTRY LETTERS | 1992年 / 07期

关键词：

D O I：

10.1246/cl.1992.1123

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In order to improve the diastereomeric excess (d.e.) in asymmetric oxyselenenylation of symmetrical cis-olefins using bis [(R)-2'-acetylamino-1,1'-binaphthalene)-2-yl] diselenide, the use of d- and 1-menthol was examined as nucleophiles. The d.e. was further enhanced for symmetrical cis-olefins as well as trans-beta-methylstyrene by using d-menthol due to double stereodifferentiation between the (R)-binaphthyl and d-menthol.

引用

页码：1123 / 1124

页数：2

共 9 条

[1]

BREWSTER JH, 1987, ALDRICHIM ACTA, V20, P3

[2] CHIRAL SYNTHESIS VIA ORGANOBORANES .10. PREPARATION OF ALPHA-CHIRAL ACYCLIC KETONES OF EXCEPTIONALLY HIGH ENANTIOMERIC EXCESS FROM OPTICALLY PURE BORINIC ESTERS [J].

BROWN, HC ;

SREBNIK, M ;

BAKSHI, RK ;

COLE, TE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5420-5426

[3] ASYMMETRIC DIHYDROXYLATION VIA LIGAND-ACCELERATED CATALYSIS [J].

JACOBSEN, EN ;

MARKO, I ;

MUNGALL, WS ;

SCHRODER, G ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (06) :1968-1970

[4] THE 1ST PRACTICAL METHOD FOR ASYMMETRIC EPOXIDATION [J].

KATSUKI, T ;

SHARPLESS, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (18) :5974-5976

[5] ASYMMETRIC-SYNTHESIS OF ISOQUINOLINE ALKALOIDS BY HOMOGENEOUS CATALYSIS [J].

NOYORI, R ;

OHTA, M ;

HSIAO, Y ;

KITAMURA, M ;

OHTA, T ;

TAKAYA, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) :7117-7119

[6] METHOXYMERCURATION OF CYCLOHEXENE [J].

ROMEYN, J ;

WRIGHT, GF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1947, 69 (03) :697-701

[7] DOUBLE DIFFERENTIATION IN ASYMMETRIC METHOXYSELENENYLATION OF TRANS-BETA-METHYLSTYRENE [J].

TOMODA, S ;

FUJITA, K ;

IWAOKA, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (02) :129-131

[8] ASYMMETRIC TRANS-ADDITION REACTIONS USING CHIRAL SELENOBINAPHTHYLS [J].

TOMODA, S ;

FUJITA, KI ;

IWAOKA, M .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1992, 67 (1-4) :247-252

[9] ASYMMETRIC TRANS-ADDITION REACTIONS OF A CHIRAL SELENOBINAPHTHYL WITH PROCHIRAL OLEFINS - THE CASE OF METHOXYSELENENYLATION [J].

TOMODA, S ;

IWAOKA, M .

CHEMISTRY LETTERS, 1988, (11) :1895-1898

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