Xiang-Guo Li, Maria Rantapaju, L. Kanerva
Mar 1, 2011
Citations
0
Influential Citations
6
Citations
Journal
European Journal of Organic Chemistry
Abstract
Kinetic resolution of three cyclic quaternary ethyl 1-amino-2,3-dihydro-1H-indene-1-carboxylates and both 1- and 2-amino-1,2,3,4-tetrahydronaphthalene analogues have been studied. Interesterification with butyl butanoate and Candida antarctica lipase B accomplished the task. The enantiomers of all 1-amino analogues reacted with excellent enantioselectivity (enantiomeric ratio er greater than 200), whereas the 2-amino analogue was not enantioselective (er = 4). Amino acid enantiomers were finally obtained as their respective hydrochlorides with almost maximum theoretical yields. For the first time, a lipase enzyme was effectively used in the kinetic resolution of cyclic α-quaternary α-amino esters.