Enantioselective propargylic [1,3]-rearrangements: copper-catalyzed O-to-N migrations toward C–N bond formation

• Published in: Chemical science (Cambridge) Vol. 8; no. 6; pp. 4299 - 4305
• Main Authors: Cheng, Li-Jie, Brown, Alexander P. N., Cordier, Christopher J.
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 2017; Royal Society of Chemistry
• Subjects: Ambient temperature; Bimetals; Binding; Bonding; Chemistry; Chemistry, Multidisciplinary; Ligands; Migration; Nitrogen; Physical Sciences; Science & Technology; Substrates; AMINATION; BETA-KETOESTERS; ALLYLIC TRANSPOSITION; 2-PYRIDONES; ALKYLATION; ESTERS; SIGMATROPIC REARRANGEMENT; DERIVATIVES; 3+2 CYCLOADDITION; ALLENYLIDENE

We have identified an enantioselective copper-catalyzed O -to- N formal [1,3]-rearrangement to form N -propargylic-2-pyridones. This enantioconvergent O -to- N propargylic rearrangement occurs rapidly at ambient temperature and high enantioselectivity is observed for a range of 3-alkyl-substituted s...