Catalysis of Ruthenium 1,2-Naphthoquinone-1-oxime Complexes towards Aldol C—C Bond Formation Reactions

Chin. J. Org. Chem. ›› 2005, Vol. 25 ›› Issue (04): 424-426. Previous Articles Next Articles

Original Articles

钌1,2-萘醌-1-肟配合物对aldol C—C成键反应的催化作用

孙克，张宝砚，刘晓霞*

(东北大学化学系沈阳 110004)

收稿日期:2004-02-27 修回日期:2004-11-10 发布日期:2005-03-30
通讯作者: 刘晓霞

Catalysis of Ruthenium 1,2-Naphthoquinone-1-oxime Complexes towards Aldol C—C Bond Formation Reactions

SUN Ke,ZHANG Bao-Yan,LIU Xiao-Xia*

(Department of Chemistry, Northeastern University, Shenyang 110004)

Received:2004-02-27 Revised:2004-11-10 Published:2005-03-30
Contact: LIU Xiao-Xia

Abstract

Aldol C—C bond formation reactions of ethyl cyanoacetate with benzaldehydes were catalyzed by ruthenium 1,2-naphthoquinone-1-oxime (1-nqo) complex, cis,cis-[Ru(1-nqo)₂(CO)(NCMe)] (1) or trans,trans- [Ru(1-nqo)₂(PBu₃)₂] (PBu₃＝tributylphosphine) (2). The reactions were monitored by GC and the products were characterized by GC-MS and ¹H NMR spectra. Except the reaction of p-formylbenzaldehyde that gave both single and double adducts, a single aldol product was detected in the catalytic reactions. ¹H NMR measurement of the purified products indicated that the stereochemistry of the products is E, showing the anti-selectivity of the catalytic reaction. The yield of 2 catalyzed reactions is higher than that of 1.

Key words: 1,2-naphthoquinone-1-oxime, C—C bond formation reaction, ruthenium

Cite this article

SUN Ke,ZHANG Bao-Yan,LIU Xiao-Xia*. Catalysis of Ruthenium 1,2-Naphthoquinone-1-oxime Complexes towards Aldol C—C Bond Formation Reactions[J]. Chin. J. Org. Chem., 2005, 25(04): 424-426.

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钌1,2-萘醌-1-肟配合物对aldol C—C成键反应的催化作用

Catalysis of Ruthenium 1,2-Naphthoquinone-1-oxime Complexes towards Aldol C—C Bond Formation Reactions

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