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Polymer‐Supported Chiral Monodentate Phosphoramidites in Palladium‐Catalyzed Allylic Alkylation Reactions
Author(s) -
Jiang ZhiDong,
Meng ZhaoHai
Publication year - 2007
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200790101
Subject(s) - chemistry , phosphoramidite , denticity , tsuji–trost reaction , ligand (biochemistry) , palladium , alkylation , allylic rearrangement , combinatorial chemistry , catalysis , polymer chemistry , organic chemistry , medicinal chemistry , metal , receptor , biochemistry , oligonucleotide , dna
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 .