ASYMMETRIC INTRAMOLECULAR DIELS-ALDER REACTIONS OF SULFOXIMINE-ACTIVATED TRIENES

被引：32

作者：

CRAIG, D ^{[1
]}

GEACH, NJ ^{[1
]}

PEARSON, CJ ^{[1
]}

SLAWIN, AMZ ^{[1
]}

WHITE, AJP ^{[1
]}

WILLIAMS, DJ ^{[1
]}

机构：

[1] RHONE POULENC AGR LTD,ONGAR CM5 0HW,ESSEX,ENGLAND

来源：

TETRAHEDRON | 1995年 / 51卷 / 21期

关键词：

D O I：

10.1016/0040-4020(95)00267-C

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of N-substituted sulfoximidoyl-1,6,8-nonatrienes and 1,7,9-decatrienes were synthesised and subjected to thermal intramolecular Diels-Alder (IMDA) reactions to give diastereomeric mixtures of substituted bicyclo[4.3.0]nonanes and -[4.4.0]decanes. The reactions showed varying selectivities. Endo/exo selectivity was interpreted in terms of a combination of steric factors and the asynchronous nature of the cycloadditions. Diastereofacial selectivity could be rationalised by considering attack by the diene on the less hindered face of the conformationally extended vinylic sulfoximine dienophile.

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页码：6071 / 6098

页数：28

相关论文

共 33 条

[1] VERY HIGH DIASTEREOFACIAL SELECTIVITY IN THE NUCLEOPHILIC EPOXIDATION OF N-(PARA-TOLYLSULPHONYL)VINYLSULPHOXIMINES [J].

BAILEY, PL ;

CLEGG, W ;

JACKSON, RFW ;

METHCOHN, O .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (01) :200-202

[2] SYNTHESIS AND HIGHLY DIASTEREOSELECTIVE NUCLEOPHILIC EPOXIDATION OF N-(P-TOLYLSULFONYL)VINYLSULFOXIMINES [J].

BAILEY, PL ;

CLEGG, W ;

JACKSON, RFW ;

METHCOHN, O .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (03) :343-350

[3] ABSOLUTE-CONFIGURATION OF A-32'287 [CONOCANDIN] AND TOTAL SYNTHESIS OF ITS METHYL AND TERT-BUTYL ESTERS [J].

BANFI, L ;

CABRI, W ;

POLI, G ;

POTENZA, D ;

SCOLASTICO, C .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (24) :5452-5457

[4] ACIDITIES OF SULFOXIMINES AND RELATED OXOSULFONIUM CATIONS - CYCLOPROPYL EFFECTS AND STRUCTURES OF ALPHA-SULFONYL-TYPE CARBANIONS [J].

BORDWELL, FG ;

BRANCA, JC ;

JOHNSON, CR ;

VANIER, NR .

JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (19) :3884-3889

[5] INTRAMOLECULAR DIELS-ALDER REACTIONS OF INTERNALLY-SUBSTITUTED TRIENYLSULFONES - SYNTHESIS OF BICYCLO[4.3.0] AND BICYCLO[4,4.0] SYSTEMS POSSESSING A BRIDGEHEAD SULFONYL GROUP [J].

CLASBY, MC ;

CRAIG, D ;

SLAWIN, AMZ ;

WHITE, AJP ;

WILLIAMS, DJ .

TETRAHEDRON, 1995, 51 (05) :1509-1532

[6] INTRAMOLECULAR DIELS-ALDER REACTIONS OF SULFONYL-SUBSTITUTED TRIENES [J].

CRAIG, D ;

FISCHER, DA ;

KEMAL, O ;

MARSH, A ;

PLESSNER, T ;

SLAWIN, AMZ ;

WILLIAMS, DJ .

TETRAHEDRON, 1991, 47 (18-19) :3095-3128

[7]

CRAIG D, 1990, SYNLETT, P531

[8] STEREOCHEMICAL ASPECTS OF THE INTRAMOLECULAR DIELS-ALDER REACTION [J].

CRAIG, D .

CHEMICAL SOCIETY REVIEWS, 1987, 16 (02) :187-238

[9]

CRAIG D, 1992, SYNLETT, P299

[10]

CRAIG D, 1993, SYNLETT, P481

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