Asymmetric synthesis of terminal N-tert-butylsulfinyl aziridines from organoceriums and an alpha-chloroimine.
Addition of N-(2-chloroethylidene)- tert-butylsulfinamide to organocerium reagents in DMPU/THF (1:10) at -78 degrees C followed by warming to 25 degrees C provides terminal N-tert-butylsulfinyl aziridines in good yields (63-92%, nine examples) and diastereomeric ratios (85:15- >99:1).
Department of Chemistry,Chemistry Research Laboratory,University of Oxford, Mansfield Road,Oxford OX1 3TA, UK. david.hodgson@chem.ox.ac.uk
David M
DM
Hodgson
Johannes
J
Kloesges
Brian
B
Evans
D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry; D002563:Cerium / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D009930:Organic Chemicals / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D001388:Aziridines; D006843:Hydrocarbons, Chlorinated; D007097:Imines; D009930:Organic Chemicals; D013457:Sulfur Compounds; C531274:alpha-chloroimine; D002563:Cerium