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Paper | Regular issue | Vol 96, No. 2, 2018, pp.219-232
Published online, 22nd January, 2018
DOI: 10.3987/COM-17-13770
Highly Regioselective Ring Opening of a Common N,N-Dialkylaziridinium Ion by Carboxylic Acids

Ulises Hernández, Manuel Velasco, Jaime Vázquez, Joel L. Terán, Dino Gnecco, María L. Orea, David M. Aparicio, and Jorge R. Juárez*

*Centro de Química, Instituto de Ciencias, Benemérita Universidad Autónoma de Puebla, Edif. IC8, Ciudad Universitaria 72570, Mexico


A variety of optically active amino esters were synthesized via ring-opening reaction of (R)-1-phenyl-3-azaspiro[2.5]octan-3-ium ion derived from (R)-2-phenyl-2-(piperidin-1-yl)ethan-1-ol in a highly regioselective manner. Ring-opening reaction with carboxylates series generated in situ proceeded smoothly and with excellent yields (85-98%).