期刊
ACS CATALYSIS
卷 9, 期 3, 页码 2169-2176出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.8b05164
关键词
enantioselective catalysis; stereodivergence; Mannich reaction; organofluorines; alpha-fluoro-beta-aminonitriles
资金
- NIH [GM106260]
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.
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