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Application of L-prolinamides as highly efficient organocatalysts for the asymmetric Michael addition of unmodified aldehydes to nitroalkenes
(Pergamon-Elsevier Science Ltd, 2012) Naziroglu, Hayriye Nevin; Durmaz, Mustafa; Bozkurt, Selahattin; Demir, Ayhan Sitki; Sirit, Abdulkadir
The asymmetric Michael addition of aldehydes to nitroolefins was investigated using a combination of L-prolinamide derivatives and various acidic additives. (S)-1,1'-Bi-2-naphthol was found to be the most effective co-catalyst and afforded the nitroaldehyde products with excellent yields (up to 95%), enantiomeric excesses (up to 99%) and diastereoselectivity ratios (up to 99:1). (C) 2012 Elsevier Ltd. All rights reserved.
Synthesis and application of L-proline and R-phenylglycine derived organocatalysts for direct asymmetric Michael addition of cyclohexanone to nitroalkenes
(Tubitak Scientific & Technological Research Council Turkey, 2012) Naziroglu, Hayriye Nevin; Sirit, Abdulkadir
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.