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Novel Enantiocomplementary C 2 ‐Symmetric Chiral Bis(imidazoline) Ligands: Highly Enantioselective Friedel–Crafts Alkylation of Indoles with Ethyl 3,3,3‐Trifluoropyruvate
Author(s) -
Nakamura Shuichi,
Hyodo Kengo,
Nakamura Yuko,
Shibata Norio,
Toru Takeshi
Publication year - 2008
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.200800189
Subject(s) - chemistry , enantioselective synthesis , imidazoline receptor , friedel–crafts reaction , enantiomer , indole test , alkylation , organic chemistry , medicinal chemistry , stereochemistry , catalysis , medicine
Enantioselective Friedel–Crafts alkylations of a variety of indoles with ethyl 3,3,3‐trifluoropyruvate catalyzed by novel chiral m ‐phenylenebis(imidazoline)‐copper(II) complexes or the bis(imidazoline)‐achiral acid combination afforded products with high enantioselectivity. Both enantiomers of indole derivatives can be prepared with high enantioselectivities by tuning the N‐substituents of the imidazoline.