Allylic C-H amination for the preparation of syn-1,3-amino alcohol motifs.
A highly selective and general Pd/sulfoxide-catalyzed allylic C-H amination reaction en route to syn-1,3-amino alcohol motifs is reported. Key to achieving this reactivity under mild conditions is the use of electron-deficient N-nosyl carbamate nucleophiles that are thought to promote functionalization by furnishing higher concentrations of anionic species in situ. The reaction is shown to be orthogonal to classical C-C bond-forming/-reduction sequences as well as nitrene-based C-H amination methods.
Rice
Grant T
GT
Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA.
White
M Christina
MC
D000475:Alkenes / Q000737:chemistry; D000586:Amination; D000605:Amino Alcohols / Q000138:chemical synthesis* / Q000737:chemistry*; D002219:Carbamates / Q000737:chemistry; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D004583:Electrons; D006859:Hydrogen / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry; D012451:Safrole / Q000031:analogs & derivatives / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
D000475:Alkenes; D000605:Amino Alcohols; D002219:Carbamates; D010165:Palladium; D002244:Carbon; D006859:Hydrogen; D012451:Safrole; C005746:sulfoxide