Ruthenium-catalyzed enantioselective prolpargylation of aromatic compounds with propargylic alcohols via allenylidene intermediates

被引：137

作者：

Matsuzawa, Hiroshi ^{[1
]}

Miyake, Yoshihiro ^{[1
]}

Nishibayashi, Yoshiaki ^{[1
]}

机构：

[1] Univ Tokyo, Sch Engn, Inst Engn Innovat, Bunkyo Ku, Tokyo 1138656, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 34期

关键词：

alkylation; asymmetric catalysis; propargylic alcohols; ruthenium; S ligands;

D O I：

10.1002/anie.200701261

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) High enantioselectivity was achieved in the Ru-catalyzed propargylation of furans and N,N-dimethylaniline derivatives to afford the propargylated aromatic compounds. This first asymmetric propargylation of aromatic compounds provides a novel protocol for the asymmetric Friedel-Crafts alkylation using propargylic alcohols as a new type of electrophile. Cp* = C5Me5. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：6488 / 6491

页数：4

共 40 条

[1] Synergistic dimetallic effects in propargylic substitution reaction catalyzed by thiolate-bridged diruthenium complex [J].

Ammal, SC ;

Yoshikai, N ;

Inada, Y ;

Nishibayashi, Y ;

Nakamura, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (26) :9428-9438

[2] New catalytic approaches in the stereoselective Friedel-Crafts alkylation reaction [J].

Bandini, M ;

Melloni, A ;

Umani-Ronchi, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (05) :550-556

[3]

Bandini M., 2004, ANGEW CHEM, V116, P560

[4] Innovative catalytic protocols for the ring-closing Friedel-Crafts-type alkylation and alkenylation of arenes [J].

Bandini, Marco ;

Emer, Enrico ;

Tommasi, Simona ;

Umani-Ronchi, Achille .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (16) :3527-3544

[5] Metal vinylidenes and allenylidenes in catalysis: Applications in anti-Markovnikov additions to terminal alkynes and alkene metathesis [J].

Bruneau, C ;

Dixneuf, PH .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (14) :2176-2203

[6]

Bruneau C., 2006, ANGEW CHEM, V118, P2232

[7] Mononuclear ruthenium catalysts for the direct propargylation of heterocycles with propargyl alcohols [J].

Bustelo, E ;

Dixneuf, PH .

ADVANCED SYNTHESIS & CATALYSIS, 2005, 347 (2-3) :393-397

[8]

Cadierno V, 2001, EUR J INORG CHEM, P571

[9]

CAFFYN AJM, 1995, COMPREHENSIVE ORGANO, V2

[10] Enantioselective Friedel-Crafts alkylations of α-β-unsaturated 2-acyl imidazoles catalyzed by bis(oxazolinyl)pyridine-scandium(III) triflate complexes [J].

Evans, DA ;

Fandrick, KR ;

Song, HJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (25) :8942-8943

← 1 2 3 4 →