Ruthenium-catalyzed carbon-carbon bond formation between propargylic alcohols and alkenes via the allenylidene-ene reaction

被引：85

作者：

Nishibayashi, Y

Inada, Y

Hidai, M ^{[1
]}

Uemura, S

机构：

[1] Kyoto Univ, Dept Energy & Hydrocarbon Chem, Sakyo Ku, Kyoto 6068501, Japan

[2] Sci Univ Tokyo, Dept Mat Sci & Technol, Noda, Chiba 2788510, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 20期

关键词：

D O I：

10.1021/ja035106j

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A novel ruthenium-catalyzed carbon-carbon bond formation between propargylic alcohols and alkenes via the allenylidene-ene reaction has been found to afford the corresponding 2,4-disubstituted-1-hexen-5-ynes in moderate yields. The finding described here discloses a new reactivity of allenylidene complexes. As a synthetic application, intramolecular cyclization of propargylic alcohols bearing an alkene moiety has been developed to give the corresponding syn-substituted chromanes in high yields with an excellent diastereoselectivity. Copyright © 2003 American Chemical Society.

引用

收藏

页码：6060 / 6061

页数：2

相关论文

共 29 条

[1] Regioselective addition of dienes to the Cβ-Cγ double bond of the allenylidene ligand of [Ru(η5-C5H5)(=C=C=CPh2)(CO)(PiPr3)]BF4 [J].

Baya, M ;

Buil, ML ;

Esteruelas, MA ;

López, AM ;

Oñate, E ;

Rodríguez, JR .

ORGANOMETALLICS, 2002, 21 (09) :1841-1848

[2] Transition metal complexes containing allenylidene, cumulenylidene, and related ligands [J].

Bruce, MI .

CHEMICAL REVIEWS, 1998, 98 (08) :2797-2858

[3] C-N and C-C coupling reactions:: Preparation of new N-heterocyclic ruthenium derivatives [J].

Buil, ML ;

Esteruelas, MA ;

López, AM ;

Oñate, E .

ORGANOMETALLICS, 2003, 22 (01) :162-171

[4] Unexpected coupling between an η5-indenyl ligand and alkenyl-vinylidene fragments:: synthesis of unprecedented (η6-indene)ruthenium(II) metallacycles [J].

Cadierno, V ;

Conejero, S ;

Díez, J ;

Gamasa, MP ;

Gimeno, J ;

García-Granda, S .

CHEMICAL COMMUNICATIONS, 2003, (07) :840-841

[5] Easy entry to terminal 1,5-and 1,6-enynes from (indenyl)ruthenium(II) allenylidenes and Grignard reagents [J].

Cadierno, V ;

Conejero, S ;

Gamasa, MP ;

Gimeno, J .

ORGANOMETALLICS, 2002, 21 (18) :3837-3840

[6]

Cadierno V, 2001, EUR J INORG CHEM, P571

[7]

CAFFYN AJM, 1995, COMPREHENSIVE ORGA 2, V12

[8] Synthesis of 2-alkoxy-5-methylenetetrahydropyrans: A regioselective ruthenium-catalyzed C-C coupling reaction of prop-2-yn-1-ols with allyl alcohol [J].

Derien, S ;

Ropartz, L ;

Le Paih, J ;

Dixneuf, PH .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3524-3531

[9]

Fürstner A, 2000, CHEM-EUR J, V6, P1847

[10] The first co-ordinatively unsaturated Group 8 allenylidene complexes:: insights into Grubbs' vs. Dixneuf-Furstner olefin metathesis catalysts [J].

Harlow, KJ ;

Hill, AF ;

Wilton-Ely, JDET .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1999, (03) :285-291