Turkish Journal of Chemistry
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.
DOI
10.3906/kim-1110-25
Keywords
Amines, asymmetric catalysis, Michael addition, nitroolefins, organocatalysis
First Page
659
Last Page
670
Recommended Citation
NAZIROĞLU, H. N, & SIRIT, A (2012). Synthesis and application of L-proline and R-phenylglycine derived organocatalysts for direct asymmetric Michael addition of cyclohexanone to nitroalkenes. Turkish Journal of Chemistry 36 (5): 659-670. https://doi.org/10.3906/kim-1110-25
