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The Asymmetric Friedel‐Crafts Reaction of Indoles with Arylidenemalonates Catalyzed by MgI 2 /PyBox Complexes
Author(s) -
Anokhin Maksim V.,
Feofanov Mikhail N.,
Averin Alexei D.,
Beletskaya Irina P.
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201703028
Subject(s) - friedel–crafts reaction , indole test , catalysis , enantioselective synthesis , reactivity (psychology) , chemistry , alkylation , copper , organic chemistry , halogen , medicinal chemistry , medicine , alkyl , alternative medicine , pathology
A mild and efficient catalytic enantioselective addition of indoles to dimethyl arylidenemalonates using MgI 2 and PyBOX ligands bearing halogen substituents has been elaborated. The reactions were conducted in DCM at low temperature generally providing high yields (up to 99%), while enantioselectivity was shown to be strongly dependent on the nature of substituents in arylidenemalonate and indole reaching 83% ee . The reactivity of arylidenemalonates under described conditions was found to be enough different from that in copper‐catalyzed Friedel‐Crafts alkylation.