Enantio- and diastereoselective catalytic alkylation reactions with aziridines.
The first asymmetric phase transfer catalyzed alkylation reaction of a range of carbon acids with N-sulfonyl aziridines is reported. When 10 mol % of a cinchona derived quaternary ammonium salt was employed as the catalyst under mildly basic conditions, N-o-(trifluoromethane)benzenesulfonyl aziridine was efficiently ring-opened to afford the amino ethylene products in consistently high yields and high enantioselectivities (up to 97% ee). By employing substituted aziridines in single enantiomeric form, the corresponding enantiopure alkylation products could be obtained with a range of pronucleophiles in high yields and moderate to high diastereoselectivities (up to 30:1 dr).
Moss
Thomas A
TA
School of Chemistry, The University of Manchester, Oxford Road, Manchester M13 9PL, UK.
Fenwick
David R
DR
Dixon
Darren J
DJ
D000478:Alkylation; D000613:Aminobutyrates / Q000138:chemical synthesis*; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D002626:Chemistry, Pharmaceutical; D000644:Quaternary Ammonium Compounds; D013237:Stereoisomerism
D000613:Aminobutyrates; D001388:Aziridines; D000644:Quaternary Ammonium Compounds