Synthesis of 1,3-amino alcohols
Enantiopure azetidinium salts were treated with various nucleophiles (azide anion, benzylamine, acetate anion or alkoxides) which provided interesting insights into the regioselectivity of the ring-opening process.
F. Couty, O. David, F. Durrat, G. Evano, S. Lakhdar, J. Marrot, M. Vargas-Sanchez, Eur. J. Org. Chem., 2006, 3479-3490.
A lewis acid-mediated highly regioselective SN2-type ring-opening of 2-aryl-N-tosylazetidines with alcohols afforded various 1,3-amino ethers in excellent yields. 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.
M. K. Ghorai, K. Das, D. Shukla, J. Org. Chem., 2007, 72, 5859-5862.