Metal-catalyzed [1,2]-alkyl shift in allenyl ketones: Synthesis of multisubstituted furans

被引：193

作者：

Dudnik, Alexander S. ^{[1
]}

Gevorgyan, Vladimir ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 27期

关键词：

allenyl ketones; furans; gold; Lewis acids; rearrangment;

D O I：

10.1002/anie.200701128

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Even fused furans can be prepared by cycloisomerization of substituted allenyl ketones. The cascade reaction involves a [1,2]-migration of alkyl or aryl groups in allenyl ketones as the key step. Facile reaction in the presence of cationic complexes, as well as migratory aptitude in the cycloisomerization of unsymmetrically substituted allenes, strongly supports an electrophilic mechanism for this transformation. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：5195 / 5197

页数：3

共 35 条

[1]

CAPOZZI G, 1976, TETRAHEDRON LETT, V17, P717

[2] THE LEWIS ACID COMPLEXES OF ALPHA,BETA-UNSATURATED CARBONYL AND NITRILE COMPOUNDS .1. A NUCLEAR MAGNETIC-RESONANCE STUDY [J].

CHILDS, RF ;

MULHOLLAND, DL ;

NIXON, A .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1982, 60 (06) :801-808

[3] THERMAL [1,5] SIGMATROPIC ALKYL SHIFTS OF ISOINDENES [J].

DOLBIER, WR ;

ANAPOLLE, KE ;

MCCULLAGH, L ;

MATSUI, K ;

RIEMANN, JM ;

ROLISON, D .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (16) :2845-2849

[4]

Ducrot P.H., 2005, COMPREHENSIVE ORGANI, V1, P375

[5] Preparation of substituted cyclopentadienes through platinum(II)-catalyzed cyclization of 1,2,4-trienes [J].

Funami, Hideaki ;

Kusama, Hiroyuki ;

Iwasawa, Nobuharu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (06) :909-911

[6] Gold(I)-catalyzed intramolecular acetylenic Schmidt reaction [J].

Gorin, DJ ;

Davis, NR ;

Toste, FD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (32) :11260-11261

[7]

Graf von der Schulenburg W, 1999, Angew Chem Int Ed Engl, V38, P1128, DOI 10.1002/(SICI)1521-3773(19990419)38:8<1128::AID-ANIE1128>3.0.CO

[8]

2-8

[9]

Hanson J. R., 1991, COMPREHENSIVE ORGANI, V3, P705

[10]

Hashmi A.S.K., 2000, ANGEW CHEM, V112, P2382, DOI DOI 10.1002/CCTC.200900237

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