Asymmetric synthesis of trans-disubstituted aryl-vinyl epoxides:: a p-methoxy effect

被引：35

作者：

Solladié-Cavallo, A ^{[1
]}

Bouérat, L ^{[1
]}

Roje, M ^{[1
]}

机构：

[1] Univ Strasbourg 1, CNRS, Lab Stereochim Organomet, ECPM, F-67087 Strasbourg, France

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 38期

关键词：

asymmetric reactions; epoxides; sulfonium salts; phosphazenes;

D O I：

10.1016/S0040-4039(00)01222-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

It was found that trans-aryl-vinyl epoxides could be synthesized with 77-100% conversion from conjugated aldehydes (which could also behave as Michael accepters and lead to cyclopropanes) and chiral sulfonium salts with ee's ranging from 95 to 100%. When a p-methoxy group was present on the arylsulfonium salt, the epoxide was the sole product whatever The solvent. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：7309 / 7312

页数：4

共 16 条

[1] Catalytic asymmetric epoxidation of aldehydes. Optimization, mechanism, and discovery of stereoelectronic control involving a combination of anomeric and Cieplak effects in sulfur ylide epoxidations with chiral 1,3-oxathianes [J].

Aggarwal, VK ;

Ford, JG ;

Fonquerna, S ;

Adams, H ;

Jones, RVH ;

Fieldhouse, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (33) :8328-8339

[2]

AGGARWAL VK, 1997, J CHEM SOC P1, V5, P593

[3] Synthesis of enantiomerically pure 2-alkyl 1-amino cyclopropane-1-carboxylic acid [J].

Calmes, M ;

Daunis, J ;

Escale, F .

TETRAHEDRON-ASYMMETRY, 1996, 7 (02) :395-396

[4] CONSTRUCTION OF RING SYSTEMS CONTAINING GEM-DIMETHYLCYCLOPROPANE UNIT USING DIPHENYLSULFONIUM ISOPROPYLIDE [J].

COREY, EJ ;

JAUTELAT, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (15) :3912-&

[5] ENANTIOSELECTIVE SYNTHESIS OF CHIRAL CARONIC ESTERS - APPLICATION TO THE SYNTHESES OF (1R)-TRANS-CHRYSANTHEMIC ACID AND ITS (1R)-CIS-DIBROMO VINYL ANALOG FROM DIMENTHYL FUMARATES [J].

DEVOS, MJ ;

KRIEF, A .

TETRAHEDRON LETTERS, 1983, 24 (01) :103-106

[6] Highly regio- and enantioselective monoepoxidation of conjugated dienes [J].

Frohn, M ;

Dalkiewicz, M ;

Tu, Y ;

Wang, ZX ;

Shi, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) :2948-2953

[7] SYNTHESIS AND PHYSICAL-PROPERTIES OF A SERIES OF OPTICALLY-ACTIVE SUBSTITUTED TRANS-STILBENE OXIDES [J].

IMUTA, M ;

ZIFFER, H .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (14) :2505-2509

[8]

ISARNO T, 2000, THESIS STRASBOURG

[9]

Lindström UM, 1998, SYNTHESIS-STUTTGART, P109

[10]

SOLIADIECAVALLO A, 1995, J ORG CHEM, V60, P3494

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