Abstract
An efficient enantioselective Friedel-Crafts alkylation reaction of indoles with α-CF3-substituted β-nitrostyrenes is disclosed. The key to success is the use of a chiral calcium BINOL bis(phosphate) complex as a Lewis acid catalyst. The reaction gives access to a wide variety of optically active indoles bearing trifluoromethylated all-carbon quaternary stereocenter (up to 20 examples) in high yields (up to 99%) with excellent enantioselectivities (up to 98%) under mild reaction conditions. Nonactivated α-alkyl-β-nitrostyrenes also participated in the Friedel-Crafts alkylation reaction successfully.
Original language | English |
---|---|
Pages (from-to) | 6903-6909 |
Number of pages | 7 |
Journal | ACS Catalysis |
Volume | 9 |
Issue number | 8 |
DOIs | |
Publication status | Published - 2019 Aug 2 |
Externally published | Yes |
Keywords
- Friedel-Crafts alkylation
- Indole
- metal chiral phosphate
- nitroalkene
- quaternary carbon center
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)