F. Palacios, A. O. D. Retana, S. Pascual
Dec 1, 2010
Citations
0
Influential Citations
19
Citations
Journal
European Journal of Organic Chemistry
Abstract
A simple and efficient synthesis of vinylogous fluoroalkylated β-amino mono- (4) and diester (9) derivatives by the regioselective 1,2-addition of enolates derived from alkyl acetates or diethyl malonate to fluoroalkylated α,β-unsaturated imines (1) is described. These fluorinated imines (1) were used as intermediates in the regioselective synthesis of fluorine-containing trans-3,4-dihydropyridin-2-ones (6, 8a, 8b, 10) and 3,3-spiro-3,4-dihydropyridin-2-ones (8c–h) by conjugate (1,4-) addition of enolates derived from α-mono- and α,α-disubstituted esters. Fluoroalkylated β-amino esters (4, 9) and 3,4-dihydropyridin-2-ones (6, 8, 10) were also prepared by the olefination of enaminophosphonate 2 with BuLi, addition of aldehydes and subsequent addition of the enolates derived from esters 3.