Polymer-Supported Chiral Monodentate Phosphoramidites in Palladium-Catalyzed Allylic Alkylation Reactions

A new and simple method for immobilization of monodentate chiral ligand on the cheap resin has been developed. A series of resin-immobilized phosphoramidite ligands based on BINOL and TADDOL backbones have been synthesized and characterized with gel-phase NMR. The immobilized ligands have been appli...

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Bibliographic Details
Published inChinese journal of chemistry Vol. 25; no. 4; pp. 542 - 545
Main Author 江志东 孟昭海
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 01.04.2007
WILEY‐VCH Verlag
Subjects
allylic alkylation
catalyst recycle
resin supported
手性单齿膦配体
烯丙基烷基化反应
聚合物负载
钯催化
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Summary:A new and simple method for immobilization of monodentate chiral ligand on the cheap resin has been developed. A series of resin-immobilized phosphoramidite ligands based on BINOL and TADDOL backbones have been synthesized and characterized with gel-phase NMR. The immobilized ligands have been applied to the Pd-catalyzed asymmetric allylic alkylation of 1,3-diphenyl-2-propenyl acetate. Among four ligands, the supported bulky monodentate phosphoramidite ligand based on TADDOL backbone afforded the chiral product with ee up to 65%; moreover, this ligand could be recycled for 3 times without substantial decrease of the conversion and ee.
Bibliography:31-1547/O6
resin supported, allylic alkylation, catalyst recycle
O621.255.8
the National Natural Science Foundation of China - No. 20148
ArticleID:CJOC200790101
istex:31D148631AF59C2AA8146E4B3A0254CB270033B3
Specialized Research Fund for the Doctoral Program of Higher Education - No. 2003058
ark:/67375/WNG-RZ7V61HS-F
Tel.: 0086‐021‐54747283; Fax: 0086‐021‐54747193
ISSN:1001-604X
1614-7065
DOI:10.1002/cjoc.200790101