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Enantioselective Friedel–Crafts Alkylation Reaction of Heteroarenes with N‐Unprotected Trifluoromethyl Ketimines by Means of Chiral Phosphoric Acid
Author(s) -
Miyagawa Masamichi,
Yoshida Masaru,
Kiyota Yuki,
Akiyama Takahiko
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201901020
Subject(s) - enantioselective synthesis , trifluoromethyl , friedel–crafts reaction , phosphoric acid , chemistry , alkylation , organic chemistry , organocatalysis , catalysis , brønsted–lowry acid–base theory , medicinal chemistry , alkyl
An enantioselective Friedel–Crafts alkylation reaction of pyrroles and indoles with N‐unprotected trifluoromethyl ketimines by use of chiral phosphoric acid provided α‐trifluoromethylated primary amines bearing chiral tetrasubstituted carbon centers in high yields and with high to excellent enantioselectivities. The present reaction is unique to N‐unprotected trifluoromethyl ketimines. No reaction took place with N‐p ‐methoxyphenyl (PMP)‐substituted ketimine. Corresponding α‐trifluoromethylated amines were transformed without loss of enantioselectivity.