A stereoselective intramolecular retro-ene reaction catalysed by aluminium chloride

被引：8

作者：

Bodajla, M ^{[1
]}

Jones, GR ^{[1
]}

Ramsden, CA ^{[1
]}

机构：

[1] UNIV KEELE, DEPT CHEM, KEELE ST5 5BG, STAFFS, ENGLAND

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 14期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(97)00404-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of 5-(2-naphthalenol)-1-pentenes with I(III) reagents results in nucleophilic substitution at C-1 rather than [4+2] intramolecular ionic cycloaddition of the proposed intermediate arenoxenium cations. Treatment of the same precursors with aluminium chloride results in a stereoselective intramolecular cyclisation to spiroketones. Evidence that the mechanism of formation involves a cyclic aluminium intermediate is presented. (C) 1997 Elsevier Science Ltd.

引用

收藏

页码：2573 / 2576

页数：4

相关论文

共 27 条

[1] STRUCTURE OF PEREZONE [J].

ARCHER, DA ;

THOMSON, RH .

CHEMICAL COMMUNICATIONS, 1965, (15) :354-&

[2]

Dewar M. J. S., 1969, MOL ORBITAL THEORY O

[3] STABILE PHENOXY-KATIONEN AUS ARYLIERTEN PHENOLEN [J].

DIMROTH, K ;

UMBACH, W ;

THOMAS, H .

CHEMISCHE BERICHTE-RECUEIL, 1967, 100 (01) :132-&

[4] REDUCTION WITH METAL HYDRIDES .12. REDUCTION OF ACETALS AND KETALS WITH LITHIUM ALUMINUM HYDRIDE-ALUMINUM CHLORIDE [J].

ELIEL, EL ;

BADDING, VG ;

RERICK, MN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (12) :2371-&

[5] ACID-CATALYZED SOLVOLYSIS OF N-SULFONYL-O-ARYLHYDROXYLAMINES AND N-ACYL-O-ARYLHYDROXYLAMINES - PHENOXENIUM IONS [J].

ENDO, Y ;

SHUDO, K ;

OKAMOTO, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (23) :6393-6397

[6] EVALUATION OF A SYNTHETIC ROUTE TO EPSILON-VINIFERIN BASED ON A NEW METHOD FOR THE STEREOSELECTIVE PREPARATION OF 2,3-DIARYL-2,3-DIHYDROBENZOFURANS [J].

ENGLER, TA ;

DRANEY, BW ;

GFESSER, GA .

TETRAHEDRON LETTERS, 1994, 35 (11) :1661-1664

[7] Studies toward the synthesis of Stemona alkaloids; A short synthesis of the tricyclic core of tuberostemonines [J].

Goldstein, DM ;

Wipf, P .

TETRAHEDRON LETTERS, 1996, 37 (06) :739-742

[8]

JKACKSON AH, 1981, J CHEM SOC P2, P286

[9] A SIMPLE SYNTHESIS OF NAPHTH[2,1-B]OXEPIN AND NAPHTH[2,1-B]OXOCIN SYSTEMS [J].

JONAS, J ;

FORREST, TP .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (03) :836-+

[10]

JONES RL, COMMUNICATION