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 : 18 | Download : 8

Publication Date : 0000-00-00

Article Type : Research Paper

Abstract :Novel R-phenylglycine derived organocatalysts were prepared from the reaction of Cbz-R-phenylglycine with indoline, pyrrolidine, or insert ignore into journalissuearticles values(S);-insert ignore into journalissuearticles values(-);-2-insert ignore into journalissuearticles values(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