Asymmetric electrophilic amination of various carbon nucleophiles with enantiomerically pure chiral N-h oxaziridines derived from camphor and fenchone.
The first two stable enantiomerically pure chiral N-H oxaziridines, derived from camphor and fenchone, are shown to act as electrophilic sources of nitrogen upon reaction with various carbon nucleophiles. Nitrogen is transferred, together with the camphor/fenchone unit, when deprotonated esters, malonates, and nitriles are used as nucleophiles. One of the ester or nitrile units in the substrate usually undergoes hydrolysis; a cyclic mechanism is proposed to account for this observation.
Bulman Page
Philip C
PC
Department of Chemistry, Loughborough University, Leicestershire LE11 3TU, England. p.c.b.page@lboro.ac.uk
Limousin
Corinne
C
Murrell
Victor L
VL
D000586:Amination; D001388:Aziridines / Q000737:chemistry*; D001892:Camphanes; D002164:Camphor / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry; D009636:Norbornanes / Q000737:chemistry*; D013237:Stereoisomerism
D001388:Aziridines; D001892:Camphanes; D004952:Esters; D009570:Nitriles; D009636:Norbornanes; C027327:fenchone; D002244:Carbon; D002164:Camphor