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Development of Diphenylamine‐Linked Bis(imidazoline) Ligands and Their Application in Asymmetric Friedel–Crafts Alkylation of Indole Derivatives with Nitroalkenes
Author(s) -
Liu Han,
Du DaMing
Publication year - 2010
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201000111
Subject(s) - chemistry , imidazoline receptor , diphenylamine , indole test , friedel–crafts reaction , alkylation , oxazoline , reagent , ligand (biochemistry) , organic chemistry , ring (chemistry) , combinatorial chemistry , medicinal chemistry , catalysis , medicine , biochemistry , receptor
The new diphenylamine‐linked bis(imidazoline) ligands were prepared through Kelly‐You’s imidazoline formation procedure mediated by Hendrickson’s reagent in good yields. The novel ligands were tested in the asymmetric Friedel–Crafts alkylation of indole derivatives with nitroalkenes. In most cases, good yields (up to 97%) and excellent enantioselectivities (up to 98%) can be achieved. The optimized bis(imidazoline) ligand with trans ‐diphenyl substitution on the imidazoline ring gave better enantioselectivity than the corresponding bis(oxazoline) ligand.