A general route for the stereoselective synthesis of (E)-(1-propenyl)phenyl esters by catalytic C=C bond isomerization

被引：18

作者：

Diaz-Alvarez, Alba E. ^{[1
]}

Crochet, Pascale ^{[1
]}

Cadierno, Victorio ^{[1
]}

机构：

[1] Univ Oviedo, Dept Quim Organ & Inorgan, IUQOEM Unidad Asociada CSIC, E-33006 Oviedo, Spain

来源：

TETRAHEDRON | 2012年 / 68卷 / 12期

关键词：

Homogeneous catalysis; Isomerization; Allylic compounds; Ruthenium; Esters; MASS SPECTROMETRIC ANALYSIS; HIGHLY EFFICIENT CATALYSTS; ESSENTIAL OILS; ALLYLIC ALCOHOLS; SELECTIVE ISOMERIZATION; CLAISEN REARRANGEMENT; AQUEOUS-MEDIA; BIS(ALLYL)-RUTHENIUM(IV) COMPLEXES; RARE PHENYLPROPANOIDS; BIOLOGICAL-ACTIVITIES;

D O I：

10.1016/j.tet.2012.01.083

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general and efficient procedure for the stereoselective synthesis of (E)-(1-propenyl)phenyl esters from readily accessible allylphenols has been developed. The process involves a two-step sequence consisting of the initial acylation of the allylphenols with an acid chloride, followed by catalytic C=C bond isomerization in the resulting allylphenyl esters. The latter step was performed in methanol at 80 degrees C using catalytic amounts (0.5 mol %) of the commercially available bis(allyl)-ruthenium(IV) dimer [{RuCl(mu-Cl)(eta(3):eta(3)-C10H16)}(2)] (C10H16=2,7-dimethylocta-2,6-diene-1,8-diyl). Reactions proceeded in high yields (68-93%) and short times (4-9 h) with complete E-selectivity. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：2611 / 2620

页数：10

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