Atom Economy in the Metathesis Cross-Coupling of Alkenes and Alkynes

被引:22
作者
Clark, Joseph R. [1 ]
Diver, Steven T. [1 ]
机构
[1] SUNY Buffalo, Dept Chem, Amherst, NY 14260 USA
基金
美国国家科学基金会;
关键词
RUTHENIUM CARBENE COMPLEXES; OLEFIN METATHESIS; ENYNE METATHESIS; TANDEM CATALYSIS; ISOMERIZATION; EFFICIENCY; MECHANISM; PHOSPHINE;
D O I
10.1021/ol200914j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A cross ene-yne metathesis has been achieved at a nearly 1:1 stoichiometry of the unsaturated reactants. This allowed the use of more complex alkene reactants without sacrificing excess alkene reactant. In the alkene, different allylic oxygen protecting groups were explored. Interestingly, alkenes containing the allylic hydroxyl group proved to be the most reactive.
引用
收藏
页码:2896 / 2899
页数:4
相关论文
共 25 条
[1]   Alkenol-alkyne cross metathesis [J].
Clark, Daniel A. ;
Clark, Joseph R. ;
Diver, Steven T. .
ORGANIC LETTERS, 2008, 10 (10) :2055-2058
[2]   Degradation of the first-generation Grubbs metathesis catalyst with primary alcohols, water, and oxygen. Formation and catalytic activity of ruthenium(II) monocarbonyl species [J].
Dinger, MB ;
Mol, JC .
ORGANOMETALLICS, 2003, 22 (05) :1089-1095
[3]   Enyne metathesis (enyne bond reorganization) [J].
Diver, ST ;
Giessert, AJ .
CHEMICAL REVIEWS, 2004, 104 (03) :1317-1382
[4]   Cyclodimerization of alkynes with phosphine-free ruthenium carbene complexes: Carbene consumption by a shunted alkyne oligomerization [J].
Diver, Steven T. ;
Kulkarni, Amol A. ;
Clark, Daniel A. ;
Peppers, Brian P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (18) :5832-+
[5]   What is amphidinolide V?: Report on a likely conquest [J].
Fuerstner, Alois ;
Larionov, Oleg ;
Fluegge, Susanne .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (29) :5545-5548
[6]   Studies on the mechanism of intermolecular enyne metathesis: Kinetic method and alkyne substituent effects [J].
Galan, BR ;
Giessert, AJ ;
Keister, JB ;
Diver, ST .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (16) :5762-5763
[7]   Impact of NHC Ligand Conformation and Solvent Concentration on the Ruthenium-Catalyzed Ring-Closing Metathesis Reaction [J].
Gatti, Michele ;
Vieille-Petit, Ludovic ;
Luan, Xinjun ;
Mariz, Ronaldo ;
Drinkel, Emma ;
Linden, Anthony ;
Dorta, Reto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (27) :9498-+
[8]   Prevention of undesirable isomerization during olefin metathesis [J].
Hong, SH ;
Sanders, DP ;
Lee, CW ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (49) :17160-17161
[9]   Some allylic substituent effects in ring-closing metathesis reactions: Allylic alcohol activation [J].
Hoye, TR ;
Zhao, H .
ORGANIC LETTERS, 1999, 1 (07) :1123-1125
[10]   Total synthesis of (-)-amphidinolide E [J].
Kim, Chan Hyuk ;
An, Hyo Jung ;
Shin, Won Kyo ;
Yu, Wei ;
Woo, Sang Kook ;
Jung, Soon Kyu ;
Lee, Eun .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (47) :8019-8021