First catalytic reductive coupling of 1,3-diynes to carbonyl partners: A new regio- and enantioselective C-C bond forming hydrogenation

被引：83

作者：

Huddleston, RR ^{[1
]}

Jang, HY ^{[1
]}

Krische, MJ ^{[1
]}

机构：

[1] Univ Texas, Dept Biochem & Chem, Austin, TX 78712 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2003年 / 125卷 / 38期

关键词：

D O I：

10.1021/ja030415v

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Upon exposure of diynes and glyoxals to cationic Rh(I) catalysts under 1 atm of hydrogen gas, regioselective condensation occurs to afford highly unsaturated enyne products without over-reduction. In the presence of chiral phosphine ligands, reductive coupling products are obtained in high enantiomeric excess at ambient temperature and pressure. The present studies are among the first examples of the electrophilic trapping of organometallic intermediates obtained transiently under the conditions of catalytic hydrogenation. Copyright © 2003 American Chemical Society.

引用

页码：11488 / 11489

页数：2

共 26 条

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[15] Branch-selective reductive coupling of 2-vinyl pyridines and imines via rhodium catalyzed C-C bond forming hydrogenation
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[16] Rhodium-catalyzed reductive cyclization of 1,6-diynes and 1,6-enynes mediated by hydrogen: Catalytic C-C bond formation via capture of hydrogenation intermediates
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[17] Enantioselective reductive cyclization of 1,6-enynes via rhodium-catalyzed asymmetric hydrogenation: C-C bond formation precedes hydrogen activation
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[18] Carbonyl propargylation from the alcohol or aldehyde oxidation level employing 1,3-enynes as surrogates to preformed allenylmetal reagents: A ruthenium-catalyzed C-C bond-forming transfer hydrogenation
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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (28) : 5220 - 5223
[19] Iridium-catalyzed C-C coupling via transfer hydrogenation: Carbonyl addition from the alcohol or aldehyde oxidation level employing 1,3-cyclohexadiene
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[20] α-hydroxy esters via enantioselective hydrogen-mediated C-C coupling:: Regiocontrolled reactions of silyl-substituted 1,3-diynes. (vol 8, pg 3874, 2006)
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