Indium-mediated γ-pentadienylation of aldehydes and ketones:: Cross-conjugated trienes for diene-transmissive cycloadditions

被引：81

作者：

Woo, S ^{[1
]}

Squires, N ^{[1
]}

Fallis, AG ^{[1
]}

机构：

[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 04期

关键词：

D O I：

10.1021/ol990695c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Treatment of 5-bromo-1,3-pentadiene with indium metal in the presence of carbonyl compounds results in gamma-pentadienylation to generate the 1,4-diene. Elimination of the resulting alcohol affords cross conjugated triene systems which rapidly react with appropriate dienophiles to give tandem intermolecular Diels-Alder adducts.

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页码：573 / 575

页数：3

相关论文

共 20 条

[1] Indium-mediated organometallic reactions in aqueous media: The nature of the allylindium intermediate [J].

Chan, TH ;

Yang, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) :3228-3229

[2] 1993 RU-LEMIEUX-AWARD-LECTURE - ORGANOMETALLIC-TYPE REACTIONS IN AQUEOUS-MEDIA - A NEW CHALLENGE IN ORGANIC-SYNTHESIS [J].

CHAN, TH ;

LI, CJ ;

LEE, MC ;

WEI, ZY .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (05) :1181-1192

[3] INTRAMOLECULAR CYCLOADDITIONS OF KETENIMINIUM SALTS - A PRACTICAL ASYMMETRIC-SYNTHESIS OF PROSTAGLANDINS [J].

CHEN, LY ;

GHOSEZ, L .

TETRAHEDRON-ASYMMETRY, 1991, 2 (12) :1181-1184

[4]

CINTAS P, 1995, SYNLETT, P1087

[5] SELECTIVE SYNTHESES WITH ORGANOMETALLICS .10. A CONVENIENT AND DIASTEREOSELECTIVE ROUTE TO HOMOALLYL ALCOHOLS - ADDITION OF (Z)-ALKENYL-DIMETHOXYBORANE OR (E)-ALKENYL-DIMETHOXYBORANE TO ALDEHYDES [J].

FUJITA, K ;

SCHLOSSER, M .

HELVETICA CHIMICA ACTA, 1982, 65 (04) :1258-1263

[6]

GERARD F, 1974, B SOC CHIM FR II-CH, P2527

[7]

GERARD F, 1974, B SOC CHIM FR II-CH, P1924

[8] INTRAMOLECULAR CYCLOADDITIONS OF KETENIMINIUM SALTS - A NOVEL-APPROACH TOWARD PROSTAGLANDINS [J].

GHOSEZ, L ;

MARKO, I ;

HESBAINFRISQUE, AM .

TETRAHEDRON LETTERS, 1986, 27 (43) :5211-5214

[9] High γ-selectivity in the coupling of penta-2,4-dienyl- and pent-2-en-4-ynylindium reagents with aldehydes [J].

Hirashita, T ;

Inoue, S ;

Yamamura, H ;

Kawai, M ;

Araki, S .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1997, 549 (1-2) :305-309

[10]

ISAAC MB, 1995, TETRAHEDRON LETT, V36, P8957