Journal
ACS CATALYSIS
Volume 9, Issue 3, Pages 2169-2176Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b05164
Keywords
enantioselective catalysis; stereodivergence; Mannich reaction; organofluorines; alpha-fluoro-beta-aminonitriles
Categories
Funding
- NIH [GM106260]
Ask authors/readers for more resources
Diastereodivergent and enantioselective conversion of isatin ketimines to alpha-fluoro-beta-aminonitriles with vicinal tetrasubstituted stereocenters is achieved by a chiral copper complex/guanidine base-catalyzed Mannich reaction with proper choice of the bisphosphine ligand. The reaction is broad in scope, scalable, and provides efficient access to a series of 3-aminoindolinones exhibiting a quaternary carbon-fluorine stereocenter with high yields and stereoselectivities. Selective transformations of the Mannich reaction products into multifunctional 3-aminooxindoles without erosion of enantiomeric and diastereomeric purity highlight the synthetic utility.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available