A two-step asymmetric synthesis of pure trans-(R,R)-diaryl-epoxides

被引：73

作者：

SolladieCavallo, A ^{[1
]}

DiepVohuule, A ^{[1
]}

Sunjic, V ^{[1
]}

Vinkovic, V ^{[1
]}

机构：

[1] RUDJER BOSKOVIC INST,DEPT ORGAN CHEM & BIOCHEM,ZAGREB 10001,CROATIA

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 06期

关键词：

D O I：

10.1016/0957-4166(96)00213-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Pure trans-(R,R)-diaryl-epoxides are obtained in two steps and under aprotic conditions using Eliel's oxathiane as the chiral auxiliary. The enantiomeric excesses, determined by chiral HPLC, are 97.9% to 99.9% and the oxathiane is recovered in 78% to 92% yield and may thus be re-used. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：1783 / 1788

页数：6

共 23 条

[1] ASYMMETRIC EPOXIDATION USING CHIRAL SULFUR YLIDES [J].

AGGARWAL, VK ;

KALOMIRI, M ;

THOMAS, AP .

TETRAHEDRON-ASYMMETRY, 1994, 5 (04) :723-730

[2] 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

[3] ASYMMETRIC-SYNTHESIS OF TRANS-2,3-DIARYLOXIRANES - BENZYLIDENE TRANSFER FROM CHIRAL ARSONIUM YLIDES [J].

ALLEN, DG ;

WILD, SB .

ORGANOMETALLICS, 1983, 2 (03) :394-399

[4]

BERTI G, 1973, TOP STEREOCHEM, V7, P221

[5] 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

[6] 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

[7]

Corey E.J., 1969, ORG SYNTH, V49, P78, DOI [10.15227/orgsyn.049.0078, DOI 10.15227/ORGSYN.049.0078]

[8] DIMETHYLSULFOXONIUM METHYLIDE [J].

COREY, EJ ;

CHAYKOVSKY, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (05) :867-&

[9] DIMETHYLSULFONIUM METHYLIDE, A REAGENT FOR SELECTIVE OXIRANE SYNTHESIS FROM ALDEHYDES AND KETONES [J].

COREY, EJ ;

CHAYKOVSKY, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (19) :3782-&

[10]

Eliel E.L., 1987, Org. Synth, V65, P215, DOI [10.15227/orgsyn.065.0215, DOI 10.15227/ORGSYN.065.0215]

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