Bifunctional reactivity of Cu(I): sequential ring opening/N-arylation.
The sequential use of a single Cu(I) catalyst enables the one-pot synthesis of N'-arylaminooxazolidinones through a Lewis acid catalyzed rearrangement followed by an N-arylation reaction. Contrary to previous reports, the formation of a cis-fused 5,5-membered ring system occurs during the rearrangement, as proven by X-ray crystallography.
Martins
Andrew
A
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.
Lemouzy
Sébastien
S
Lautens
Mark
M
D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry
D009942:Organometallic Compounds; D023303:Oxazolidinones; D003300:Copper