TY - JOUR
TI - Synthesis of homoproline analogues containing heterocyclic rings and their activity as organocatalysts for Michael reaction
AU - Barbayianni, E.
AU - Bouzi, P.
AU - Constantinou-Kokotou, V.
AU - Ragoussis, V.
AU - Kokotos, G.
JO - Heterocycles
PY - 2009
VL - 78
TODO - 5
SP - 1243-1252
PB - 
SN - 0385-5414, 1881-0942
TODO - 10.3987/COM-08-11620
TODO - null
TODO - Two homoproline derivatives containing either the 5-thioxo-1,2,4-oxadiazole or the 2-oxo-1,2,3,5-oxathiodiazole bioisosteric groups, in replacement of the carboxyl group, were synthesized and their catalytic activities in Michael reactions were evaluated. The derivative containing the 5-thioxo-1,2,4-oxadiazole ring outperforms proline in the context of enantioselectivity in the reactions between β-nitrostyrene and acetone or cyclohexanone, indicating that the conversion of the carboxylic group of homoproline to a bioisosteric heterocyclic ring leads to a superior organocatalyst. © 2009 The Japan Institute of Heterocyclic Chemistry All rights reserved.
ER -