Diels-Alder reactions of [(S)R]-(1E,3E)-1-p-tolylsulfinyl-1,3-pentadiene: The unexpected evolution of maleic anhydride adducts.

被引：26

作者：

Carreno, MC

Cid, MB

Ruano, JLG

机构：

[1] Depto. de Quimica Organica (C-I), Universidad Autónoma, Cantoblanco

来源：

TETRAHEDRON-ASYMMETRY | 1996年 / 7卷 / 07期

关键词：

D O I：

10.1016/0957-4166(96)00258-3

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The Diels-Alder adducts resulting in the reaction of enantiomerically pure [(S)R]-(1E,3E)-1-p-tolylsulfinyl-1,3-pentadiene with maleic anhydride evolved stereoselectively in situ through several intramolecular tandem reactions, involving [2,3]-sigmatropic sulfoxide-sulfenate rearrangement, acylation of the sulfinyl oxygen, and elimination of the sulfur function through a S(N)2' process yielding lactones 3 and 4. Copyright (C) 1996 Elsevier Science Ltd

引用

收藏

页码：2151 / 2158

页数：8

相关论文

共 20 条

[1] FIRST DIELS-ALDER REACTIONS OF ENANTIOMERICALLY PURE 1-P-TOLYLSULFINYL DIENES - STRAIGHTFORWARD ACCESS TO CYCLOHEXENOLS THROUGH TANDEM CYCLOADDITION [2,3]-SIGMATROPIC REARRANGEMENT [J].

ARCE, E ;

CARRENO, MC ;

CID, MB ;

RUANO, JLG .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3421-3426

[2] A PRACTICAL SYNTHESIS OF THE ANTITUMOR AGENT 2-METHYL-4-DEOXYISOPICROPODOPHYLLOTOXIN AND RELATED PODOPHYLLIN ANALOGS [J].

BEARD, AR ;

HAZELL, SJ ;

MANN, J ;

PALMER, C .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (11) :1235-1238

[3]

Bersch W., 1928, ARCH PHARM BER DTSCH, V266, P697

[4]

Braverman S., 1988, CHEM SULPHONES SULPH, P717

[5]

BRUCKENER R, 1991, COMPREHENSIVE ORGANI, V6, P899

[6] STEREOSELECTIVE REDUCTIONS OF 2-KETO SULFOXIDES WITH HYDRIDES [J].

CARRENO, MC ;

RUANO, JLG ;

MARTIN, AM ;

PEDREGAL, C ;

RODRIGUEZ, JH ;

RUBIO, A ;

SANCHEZ, J ;

SOLLADIE, G .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :2120-2128

[7] DIELS-ALDER REACTIONS OF 1-SULFINYLDIENES WITH AN ENDOCYCLIC DOUBLE-BOND - THE UNEXPECTED EVOLUTION OF THE N-METHYLMALEIMIDE ADDUCTS [J].

CARRENO, MC ;

CID, MB ;

COLOBERT, F ;

RUANO, JLG ;

SOLLADIE, G .

TETRAHEDRON-ASYMMETRY, 1994, 5 (08) :1439-1442

[8]

Diels O, 1928, LIEBIGS ANN CHEM, V460, P98

[9] COMPLEMENTARITY OF (4+2) CYCLOADDITION REACTIONS AND [2,3] SIGMATROPIC REARRANGEMENTS IN SYNTHESIS - NEW SYNTHESIS OF FUNCTIONALIZED HASUBANAN DERIVATIVES [J].

EVANS, DA ;

SIMS, CL ;

BRYAN, CA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (08) :2891-&

[10] FACE SELECTIVITY IN DIELS-ALDER REACTIONS OF CHIRAL DIENES CONTAINING ALLYLIC SUBSTITUENTS [J].

FISHER, MJ ;

HEHRE, WJ ;

KAHN, SD ;

OVERMAN, LE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) :4625-4633