H. Ohkura, Dmitrii O. Berbasov, V. Soloshonok
Mar 10, 2003
Citations
0
Influential Citations
26
Citations
Journal
Tetrahedron Letters
Abstract
Abstract The reaction between 1,1,1,5,5,5-hexafluoro-2,4-pentanedione and 2-(aminomethyl)pyridine, or its salts with carboxylic acids, was found to produce a mixture of diastereomeric 2-(2′-pyridyl)-3-hydroxy-3,5-bis-trifluoromethyl-1-pyrrolines with high (up to 85% de) of kinetic (3 R* ,5 S* )-diastereoselectivity. The thermodynamic (3 R* ,5 R* ) diastereomer was prepared as a major product (90% de) by epimerization of the kinetic (3 R* ,5 S* ) diastereomer with triethylamine.