A third generation chiral phosphorus-containing dendrimer as ligand in Pd-catalyzed asymmetric allylic alkylation

被引：43

作者：

Laurent, R ^{[1
]}

Caminade, AM ^{[1
]}

Majoral, JP ^{[1
]}

机构：

[1] CNRS, Chim Coordinat Lab, F-31077 Toulouse, France

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 38期

关键词：

dendrimer; asymmetric catalysis; allylic alkylation; phosphorus;

D O I：

10.1016/j.tetlet.2005.07.100

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a third generation phosphorus-containing dendrimer possessing 24 chiral iminophosphine end groups derived from (2S)-2-amino-1-(diphenylphosphinyl)-3-methylbutane is described. In situ complexation of this dendrimer by [Pd(eta(3)-C3H5)Cl](2) affords a catalyst, which is used in asymmetric allylic alkylations of rac-(E)-diphenyl-2-propenyl acetate and pivalate. The percentage of conversion, the yield of isolated 2-(1,3-diphenylallyl)-malonic acid dimethyl ester, and its enantiomeric excess have been measured in each case, and were found to be good to very good (ee from 90% to 95%). Furthermore, the dendritic catalyst can be recovered and reused at least two times, with almost the same efficiency. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：6503 / 6506

页数：4

共 44 条

[1] Investigation of the importance of nitrogen substituents in a N-P chiral ligand for enantioselective allylic alkylation [J].