1. Toward a Catalytic Atroposelective Synthesis of Diaryl Ethers Through C(sp2)–H Alkylation with Nitroalkanes
- Author
-
Jeffrey L. Gustafson, Andrew N. Dinh, Sean T. Toenjes, Amy C. Jackson, Sean M. Maddox, Mirza A. Saputra, and Ryan R. Noorbehesht
- Subjects
Steric effects ,chemistry.chemical_classification ,Atropisomer ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,Enantioselective synthesis ,Alkylation ,010402 general chemistry ,01 natural sciences ,Medicinal chemistry ,0104 chemical sciences ,Catalysis ,chemistry.chemical_compound ,Urea ,Chirality (chemistry) ,Alkyl - Abstract
We report studies toward a small-molecule-catalytic approach to access atropisomeric diaryl ethers that proceeds through a C(sp2)–H alkylation using nitroalkanes as the alkyl source. A quaternary ammonium salt derived from quinine, containing a sterically hindered urea at the C-9 position, was found to effect atroposelective C(sp2)–H alkylation with moderate to good enantioselectivities across several naphthoquinone-containing diaryl ethers. Products could then be isolated in >95:5 er after one round of trituration. For several substrates that were evaluated, we obtained nitroethylated products in similar yields and selectivities.
- Published
- 2018
- Full Text
- View/download PDF