@article{3062127, title = "Synthesis of homoproline analogues containing heterocyclic rings and their activity as organocatalysts for Michael reaction", author = "Barbayianni, E. and Bouzi, P. and Constantinou-Kokotou, V. and Ragoussis, V. and Kokotos, G.", journal = "Heterocycles", year = "2009", volume = "78", number = "5", pages = "1243-1252", issn = "0385-5414, 1881-0942", doi = "10.3987/COM-08-11620", abstract = "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." }