Ruthenium-catalyzed allylic substitution of cyclic allyl carbonates with nucleophiles. Stereoselectivity and scope of the reaction

被引：93

作者：

Morisaki, Y ^{[1
]}

Kondo, T ^{[1
]}

Mitsudo, TA ^{[1
]}

机构：

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

来源：

ORGANOMETALLICS | 1999年 / 18卷 / 23期

关键词：

D O I：

10.1021/om990533k

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

CpRuCl(cod)/NH4PF6 (Cp = cyclopentadienyl, cod = 1,5-cyclooctadiene) is an effective catalyst system for the allylic substitution of cyclic allyl carbonates with nucleophiles. This catalyst system enables the first investigation of the stereochemical course of the ruthenium-catalyzed allylic substitution reaction, in which the reaction proceeds with an overall retention of configuration. The stoichiometric reaction of trans-5-(methoxycarbonyl)cyclohex-2-enyl chloride with Cp*RuCl(cod) (Cp* = pentamethylcyclopentadienyl) gave the unexpected complex Cp*Ru(eta(6)-C6H5CO2Me)(+) by the rapid dehydrohalogenation/dehydrogenation of the desired Cp*RuCl2-(eta(3)-C6H8CO2Me) complex.

引用

页码：4742 / 4746

页数：5

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