Lewis acid-mediated highly regioselective SN2-Type ring-opening of 2-aryl-N-tosylazetidines and aziridines by alcohols.
Lewis acid-mediated highly regioselective SN2-type ring-opening of 2-aryl-N-tosylazetidines with alcohols to afford various 1,3-amino ethers in excellent yields with good enantiomeric excess is described. Similar SN2-type ring-opening of chiral 2-phenyl-N-tosylaziridine with various alcohols produces the corresponding nonracemic 1,2-amino ethers in excellent yields and good ee. The mechanism of the ring-opening of aziridines and azetidines via an SN2 pathway is supported by the formation of nonracemic amino ethers.
Ghorai
Manas K
MK
Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India. mkghorai@iitk.ac.in
Das
Kalpataru
K
Shukla
Dipti
D