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Synthesis of a novel photoresponsive axially chiral phosphine ligand containing an arylazo group and its application to palladium‐catalyzed asymmetric allylic alkylation
Author(s) -
Kawamura Masato,
Kiyotake Ryosuke,
Kudo Kazuaki
Publication year - 2002
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.10131
Subject(s) - chemistry , tsuji–trost reaction , azobenzene , photoisomerization , palladium , alkylation , moiety , ligand (biochemistry) , phosphine , catalysis , enantiomeric excess , allylic rearrangement , photochemistry , medicinal chemistry , stereochemistry , isomerization , enantioselective synthesis , organic chemistry , receptor , biochemistry , molecule
Novel photoresponsive axially chiral monophosphine ligands containing azobenzene moiety were prepared and applied to a palladium‐catalyzed allylic alkylation. The reaction of rac ‐1,3‐diphenyl‐2‐propenyl acetate gave the alkylated products with up to 90% enantiomeric excess. The ligand exhibited a trans to cis photoisomerization upon irradiation with UV light. Chirality 14:724–726, 2002. © 2002 Wiley‐Liss, Inc.