Synthesis and application of L-proline and R-phenylglycine derived organocatalysts for direct asymmetric Michael addition of cyclohexanone to nitroalkenes

Authors

HAYRİYE NEVİN NAZIROĞLU
ABDULKADİR SIRIT

DOI

10.3906/kim-1110-25

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

First Page

659

Last Page

670

Recommended Citation

NAZIROĞLU, HAYRİYE NEVİN and SIRIT, ABDULKADİR (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: Vol. 36: No. 5, Article 2. https://doi.org/10.3906/kim-1110-25
Available at: https://journals.tubitak.gov.tr/chem/vol36/iss5/2