New developments in the Pd-catalysed cyclisation-coupling reaction of alkene-containing carbonucleophiles with organic halides (and triflates).: The first examples of asymmetric catalysis

被引：4

作者：

Bruyère, D ^{[1
]}

Monteiro, N ^{[1
]}

Bouyssi, D ^{[1
]}

Balme, G ^{[1
]}

机构：

[1] Univ Lyon 1, CNRS, UMR 5622, Lab Chim Organ 1, F-69622 Villeurbanne, France

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2003年 / 687卷 / 02期

关键词：

asymmetric catalysis; palladium; P ligands; carbocyclisations;

D O I：

10.1016/S0022-328X(03)00700-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The results of our preliminary investigations directed toward asymmetric catalysis of the cyclocarbopalladation of alkenes bearing a proximate nucleophile with organic halides (or triflates) are disclosed. A series of bidentate phosphine ligands were evaluated in intramolecular versions of this reaction using (E)-2-[7-(2-bromophenyl)-hept-4-enyl]-malonic acid dimethyl ester (1) and (Z)-2-[7-(2-trifluoromethanesulfonyloxy-phenyl)-hept-4-enyl]-malonic acid dimethyl ester (9) as model substrates. The highest enantioselective induction was obtained with aryl triflate 9 which produced the corresponding cyclopentylindane as a single diastereomer in 54% chemical yield and 43% ee by using PdCl2[S-(-)-TolBINAP] as chiral catalyst and K2CO3 as base. (C) 2003 Elsevier B.V. All rights reserved.

引用

页码：466 / 472

页数：7