Fluoroalkylated alpha,beta-Unsaturated Imines: Efficient and Versatile Substrates for the Synthesis of Fluorinated Vinylogous beta-Amino Esters and 3,4-Dihydropyridin-2-ones

[摘要]：A simple and efficient synthesis of vinylogous fluoroalkylated beta-amino mono- (4) and diester (9) derivatives by the regioselective 1,2-addition of enolates derived from alkyl acetates or diethyl malonate to fluoroalkylated alpha,beta-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 alpha- mono-and alpha,alpha-disubstituted esters. Fluoroalkylated beta-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.

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