A NOVEL STEREOSELECTIVE ROUTE TO GAMMA-BUTYROLACTONES

被引：33

作者：

CASEY, M

MANAGE, AC

MURPHY, PJ

机构：

[1] Department of Chemistry and Applied Chemistry, University of Salford, Salford

来源：

TETRAHEDRON LETTERS | 1992年 / 33卷 / 07期

关键词：

LACTONES; TETRAHYDROFURANS; CONJUGATE ADDITIONS; SULFOXIDES; STEREOSELECTIVE;

D O I：

10.1016/S0040-4039(00)91589-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of the products obtained from conjugate additions of sulfoxides to alpha,beta-unsaturated carbonyl compounds with soft electrophiles resulted in intramolecular displacement of the sulfinyl group by the carbonyl to give gamma-butyrolactones. This novel cyclisation works best for benzylic sulfoxides and provides a concise route to trans-beta,gamma-disubstituted lactones with high stereoselectivity.

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页码：965 / 968

页数：4

相关论文

共 13 条

[1] SYNTHESIS OF THE (4S,5R)-5-HYDROXY-DECAN-4-OLIDE (L-FACTOR) AND OF THE (R)-DECAN-4-OLIDE FROM A CHIRAL SULFOXIDE [J].

BRAVO, P ;

RESNATI, G ;

VIANI, F ;

ARNONE, A .

TETRAHEDRON, 1987, 43 (20) :4635-4647

[2] STEREOSELECTIVE CONJUGATE ADDITIONS OF SULFOXIDE STABILIZED CARBANIONS TO ALPHA,BETA-UNSATURATED ESTERS [J].

CASEY, M ;

MANAGE, AC ;

NEZHAT, L .

TETRAHEDRON LETTERS, 1988, 29 (45) :5821-5824

[3] STEREOSELECTIVE CONJUGATE ADDITIONS OF BENZYL SULFOXIDES TO ALPHA,BETA-UNSATURATED ESTERS [J].

CASEY, M ;

MANAGE, AC ;

GAIRNS, RS .

TETRAHEDRON LETTERS, 1989, 30 (49) :6919-6922

[4]

CASEY ML, UNPUB

[5] CONFORMATIONAL-ANALYSIS AND FLEXIBILITY OF BULKY 2-ARYL TETRAHYDROFURANS STUDIED USING NMR AND MOLECULAR MECHANICS [J].

DANA, G ;

TOUBOUL, E ;

CONVERT, O ;

PASCAL, YL .

TETRAHEDRON, 1988, 44 (02) :429-442

[6]

FARNUM DG, 1977, TETRAHEDRON LETT, P4009

[7] MANGANESE(III)-MEDIATED GAMMA-LACTONE ANNULATION [J].

FRISTAD, WE ;

PETERSON, JR .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (01) :10-18

[8] CHEMISTRY OF SULFOXIDES AND RELATED COMPOUNDS .34. MECHANISM OF SULFONIUM YLIDE REACTIONS - SYNTHESIS OF CYCLOPROPANES AND OXIRANES OF HIGH OPTICAL PURITY [J].

JOHNSON, CR ;

SCHROECK, CW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (20) :5303-&

[9] GLYCOSYLATION OF UNREACTIVE SUBSTRATES [J].

KAHNE, D ;

WALKER, S ;

CHENG, Y ;

VANENGEN, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) :6881-6882

[10] ABSOLUTE-CONFIGURATIONS OF QUERCUS LACTONES, (3S,4R)-3-METHYL-4-OCTANOLIDE AND (3S,4S)-3-METHYL-4-OCTANOLIDE, FROM OAK WOOD AND CHIROPTICAL PROPERTIES OF MONOCYCLIC GAMMA-LACTONES [J].

MASUDA, M ;

NISHIMURA, K .

CHEMISTRY LETTERS, 1981, (10) :1333-1336