SYNTHESIS AND STEREOCHEMISTRY OF OPTICALLY-ACTIVE SELENOXIDES

被引：9

作者：

KAMIGATA, N

SHIMIZU, T

机构：

[1] Department of Chemistry, Faculty of Science, Tokyo Metropolitan University

来源：

JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN | 1990年 / 48卷 / 03期

关键词：

D O I：

10.5059/yukigoseikyokaishi.48.229

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Some optically active diaryl selenoxides stabilized by bulky oitho substituents such as isopropyl or t-butyl group were obtained by fractionary recrystallization or by chromatographic resolutions. Optically active alkyl aryl selenoxides were synthesized by asymmetric oxidation of corresponding selenides under Sharpless oxidation conditions The absolute configurations of these optically active selenoxides were determined by X-ray diffraction and circular dichroism spectra. The rate of racemization of the optically active selenoxide under several conditions were investigated, and the mechanism involving achiral hydrate was clarified by H218Ostudies. © 1990, The Society of Synthetic Organic Chemistry, Japan. All rights reserved.

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页码：229 / 239

页数：11

相关论文

共 32 条

[1] STUDIES OF ENAMIDIC DELTA-5-4-AZASTEROIDAL SELENOXIDES - PREPARATION, PUMMERER REACTIONS, CONFIGURATIONAL STABILITY, AND CONVERSION TO CARBINOL AMIDES [J].

BACK, TG ;

IBRAHIM, N ;

MCPHEE, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (17) :3283-3289

[2]

DALLING DK, 1971, J AM CHEM SOC, V93, P3678

[3] ASYMMETRIC OXIDATION OF ACHIRAL SELENIDES TO OPTICALLY-ACTIVE SELENOXIDES - STEREOCHEMISTRY OF THE ALLYL SELENOXIDE-SELENATE [2,3] SIGMATROPIC REARRANGEMENT [J].

DAVIS, FA ;

STRINGER, OD ;

MCCAULEY, JP .

TETRAHEDRON, 1985, 41 (21) :4747-4757

[4] 1ST SYNTHESIS OF SIMPLE OPTICALLY-ACTIVE SELENOXIDES [J].

DAVIS, FA ;

BILLMERS, JM ;

STRINGER, OD .

TETRAHEDRON LETTERS, 1983, 24 (31) :3191-3194

[5] The quadrivalency of selenium - Part II The simple halogen derivatives and the dihydroxide of 4-acetamidodiphenyl selenide [J].

Gaythwaite, WR ;

Kenyon, J ;

Phillips, H .

JOURNAL OF THE CHEMICAL SOCIETY, 1928, :2287-2293

[6] The quadrivalency of selemum - Part I 4-carboxydiphenyl and p-carboxyphenyl methyl selenoxides [J].

Gaythwaite, WR ;

Kenyon, J ;

Phillips, H .

JOURNAL OF THE CHEMICAL SOCIETY, 1928, :2280-2287

[7] THE SYNTHETIC APPLICATION OF ORTHO-BETA-BROMOETHYLBENZYL BROMIDE .5. THE PREPARATION AND PROPERTIES OF THIOISOCHROMAN, SELENOISOCHROMAN, TELLUROISOCHROMAN, AND OF THEIR OPTICALLY ACTIVE DERIVATIVES [J].

HOLLIMAN, FG ;

MANN, FG .

JOURNAL OF THE CHEMICAL SOCIETY, 1945, (JAN-) :37-44

[8] STEROIDAL SELENOXIDES DIASTEREOISOMERIC AT SELENIUM . SYN-ELIMINATION, ABSOLUTE CONFIGURATION, AND OPTICAL ROTATORY DISPERSION CHARACTERISTICS [J].

JONES, DN ;

MUNDY, D ;

WHITEHOUSE, RD .

JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1970, (02) :86-+

[9] SYNTHESIS OF SELENOXIDES BY OXIDATION OF SELENIDES WITH TERT-BUTYL HYPOCHLORITE, AND ITS APPLICATION FOR SYNTHESIS OF OPTICALLY-ACTIVE SELENOXIDE [J].

KOBAYASHI, M ;

OHKUBO, H ;

SHIMIZU, T .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1986, 59 (02) :503-506

[10] ASYMMETRIC INDUCTION IN THE ALKYLATION OF ENOLATE ANION WITH THE OPTICALLY-ACTIVE SELENONIUM IONS [J].

KOBAYASHI, M ;

KOYABU, K ;

SHIMIZU, T ;

UMEMURA, K ;

MATSUYAMA, H .

CHEMISTRY LETTERS, 1986, (12) :2117-2120

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