Scalable synthesis of N-acylaziridines from N-tosylaziridines.
N-Acylaziridines are important starting materials for the synthesis of chiral amine derivatives. The traditional methods for producing these activated aziridines have significant drawbacks. The gram scale synthesis of N-acylaziridines by deprotection of N-tosylaziridines and reprotection with N-hydroxysuccinimide derivatives is described. Mono- and disubstituted aziridines perform well, with complete retention of stereochemical purity. The consistently moderate yields are linked to the N-tosylaziridine deprotection step, while acylation with N-hydroxysuccinimide derivatives is highly efficient.
Department of Chemistry and Biochemistry, University of North Carolina Wilmington, Dobo Hall, Wilmington, North Carolina 28403, USA.
Heather
H
Rubin
Jennifer
J
Cockrell
Jeremy B
JB
Morgan
D001388:Aziridines / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D014105:Tosyl Compounds / Q000737:chemistry*
D001388:Aziridines; D014105:Tosyl Compounds