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- Title
Enantioselective Friedel–Crafts Alkylation Reaction of Heteroarenes with N‐Unprotected Trifluoromethyl Ketimines by Means of Chiral Phosphoric Acid.
- Authors
Miyagawa, Masamichi; Yoshida, Masaru; Kiyota, Yuki; Akiyama, Takahiko
- Abstract
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.
- Subjects
FRIEDEL-Crafts reaction; IMINES; PHOSPHORIC acid; HETEROARENES; INDOLE compounds; AMINES
- Publication
Chemistry - A European Journal, 2019, Vol 25, Issue 22, p5677
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201901020