Novel 1,3-diene synthesis from alkyne and ethylene by ruthenium-catalyzed enyne metathesis

被引:94
作者
Kinoshita, A [1 ]
Sakakibara, N [1 ]
Mori, M [1 ]
机构
[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
关键词
enyne metathesis; diene; ruthenium; metathesis; alkyne metathesis; ethylene;
D O I
10.1016/S0040-4020(99)00297-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel 1,3-diene synthetic method from alkyne and ethylene was developed using ruthenium-catalyzed enyne metathesis. The reaction procedure is very simple: A CH2Cl2 solution of alkyne was stirred at room temperature under ethylene gas (1 atm.) in the presence of a catalytic amount of ruthenium benzylidene complex. The yield was good and the conversion yield was high. Dienes having functional groups such as a keto-carbonyl group, silyloxy group, ester, and ketal were synthesized from the corresponding alkynes and ethylene. In this reaction, the alkyne having a hetero atom at the propargylic position gave a good result and ether oxygen or amine nitrogen that coordinate strongly to the ruthenium catalyst prevents the reaction. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8155 / 8167
页数:13
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