- Turkish Journal of Chemistry
- Vol: 36 Issue: 5
- Synthesis and application of L-proline and R-phenylglycine derived organocatalysts for direct asymme...
Synthesis and application of L-proline and R-phenylglycine derived organocatalysts for direct asymmetric Michael addition of cyclohexanone to nitroalkenes
Authors : Hayriye Nevin Naziroğlu, Abdulkadir Sirit
Pages : 659-670
Doi:10.3906/tar-1301-69
View : 11 | Download : 5
Publication Date : 9999-12-31
Article Type : Makaleler
Abstract :Novel R-phenylglycine derived organocatalysts were prepared from the reaction of Cbz-R-phenylglycine with indoline, pyrrolidine, or (S)-(-)-2-(diphenylmethyl)pyrrolidine in 3 steps. The asymmetric Michael addition of cyclohexanone to nitroolefins was investigated using R-phenylglycine derivatives along with L-prolinamides as chiral catalysts. The desired products were obtained in excellent yields with enantioselectivities up to 90% ee and diastereomeric ratio up to 98:2 of the syn }addition product.Keywords : Amines, asymmetric catalysis, Michael addition, nitroolefins, organocatalysis