Terminal aziridines by alpha-deprotonation/electrophile trapping of N-protected aziridine.
N-tert-Butylsulfonyl and N-tert-butylsulfinyl aziridine undergo alpha-lithiation/electrophile trapping providing a new entry to terminal aziridines. With N-tert-butylsulfinyl aziridine complete asymmetric induction is observed alpha to nitrogen.
Hodgson
David M
DM
Department of Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. david.hodgson@chem.ox.ac.uk
Hughes
Steven P
SP
Thompson
Amber L
AL
Heightman
Tom D
TD
D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry; D015394:Molecular Structure; D011522:Protons; D013237:Stereoisomerism
D001388:Aziridines; D011522:Protons; D008094:Lithium