A. Studer et al., FLUOROUS SYNTHESIS - FLUOROUS PROTOCOLS FOR THE UGI AND BIGINELLI MULTICOMPONENT CONDENSATIONS, Journal of organic chemistry, 62(9), 1997, pp. 2917-2924
A new protocol for multicomponent condensation reactions that uses flu
orous (highly fluorinated) substrates is introduced. This method takes
advantage of the ease of purification of fluorous compounds by liquid
-liquid extractions between fluorous and organic solvents. The applica
tion of this method to the Ugi and Biginelli reactions is described. T
he condensation products of these two reactions, amino acid amides and
dihydropyrimidines, are easily obtained without chromatography in hig
h purities, even though the other reagents are used in very large exce
sses. This is. the first demonstration of the suitability of fluorous
phase methods for combinatorial synthesis of ''druglike'' organic mole
cules.