ASYMMETRIC-SYNTHESIS OF EPOXIDES USING CHIRAL SULFIMIDES

被引：32

作者：

BAIRD, CP ^{[1
]}

TAYLOR, PC ^{[1
]}

机构：

[1] UNIV WARWICK,DEPT CHEM,COVENTRY CV4 7AL,W MIDLANDS,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1995年 / 08期

关键词：

D O I：

10.1039/c39950000893

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The sodium salt of (S)-sulfimide 8 reacts with carbonyl compounds to yield (R)-epoxides in 60-64% yield and 21-70% e.e.

引用

页码：893 / 894

页数：2

共 22 条

[1] NOVEL CATALYTIC CYCLE FOR THE SYNTHESIS OF EPOXIDES FROM ALDEHYDES AND SULFUR YLIDES MEDIATED BY CATALYTIC QUANTITIES OF SULFIDES AND RH-2(OAC)(4) [J].

AGGARWAL, VK ;

ABDELRAHMAN, H ;

JONES, RVH ;

LEE, HY ;

REID, BD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (13) :5973-5974

[2] PREPARATION OF OPTICALLY-ACTIVE EPOXIDES VIA SULFUR YLIDES - ORIGIN OF THE CHIRAL INDUCTION [J].

BREAU, L ;

DURST, T .

TETRAHEDRON-ASYMMETRY, 1991, 2 (05) :367-370

[3] PREPARATION OF OPTICALLY-ACTIVE STILBENE OXIDES VIA SULFONIUM SALTS DERIVED FROM C-2 SYMMETRIC THIOLANES [J].

BREAU, L ;

OGILVIE, WW ;

DURST, T .

TETRAHEDRON LETTERS, 1990, 31 (01) :35-38

[4] ENANTIOSELECTIVE EPOXIDATION OF CYCLIC 1,3-DIENES CATALYZED BY A STERICALLY AND ELECTRONICALLY OPTIMIZED (SALEN)MN COMPLEX [J].

CHANG, S ;

HEID, RM ;

JACOBSEN, EN .

TETRAHEDRON LETTERS, 1994, 35 (05) :669-672

[5] STEREOCHEMISTRY OF SULFUR COMPOUNDS .1. STEREOCHEMICAL REACTION CYCLES INVOLVING AN OPEN CHAIN SULFOXIDE, SULFIMIDE, AND SULFOXIMIDE [J].

CRAM, DJ ;

DAY, J ;

RAYNER, DR ;

SCHRILTZ, DM ;

DUCHAMP, DJ ;

GARWOOD, DC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (25) :7369-&

[6] CAMPHORYL SULFIDE AS A CHIRAL AUXILIARY AND A MEDIATOR FOR ONE-STEP SYNTHESIS OF OPTICALLY-ACTIVE 1,2-DIARYLOXIRANES [J].

FURUKAWA, N ;

SUGIHARA, Y ;

FUJIHARA, H .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (17) :4222-4224

[7]

GILCHRIST TL, 1977, CHEM REV, P409

[8] PREPARATION AND REACTIONS OF N-(PARA-TOLYLSULFONYL)SULFILIMINES [J].

JOHNSON, CR ;

MORI, K ;

NAKANISHI, A .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (13) :2065-2067

[9] SYNTHESIS OF OPTICALLY ACTIVE CYCLOPROPANES AND OXIRANES USING AN OPTICALLY ACTIVE OXOSULFONIUM METHYLIDE [J].

JOHNSON, CR ;

SCHROECK, CW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (24) :6852-&

[10] CHEMISTRY OF SULFOXIDES AND RELATED COMPOUNDS .42. NUCLEOPHILIC ALKYLIDENE TRANSFER REAGENTS - ANIONS OF N-(PARA TOLYLSULFONYL)SULFOXIMINES [J].

JOHNSON, CR ;

KIRCHHOF.RA ;

REISCHER, RJ ;

KATEKAR, GF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (13) :4287-4291

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