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Synthesis of New Di- and Triamides as Potential Organocatalysts for Asymmetric Aldol Reaction in Water

Elif Keskin, Cigdem Yolacan, Feray Aydogan

Abstract


New di- or triamide organocatalysts derived from (L)-proline were synthesized and successfully used in the direct asymmetric aldol reaction of aliphatic ketones and aromatic aldehydes in water at 0oC in the presence of benzoic acid as co-catalyst. (S)-methyl-2-((S)-3-hydroxy-2-((S)-3-pyrrolidine-2-carboxamido)propanamido)-3-phenylpropanoate (7c) as organocatalyst showed best results under these reaction conditions, and good diastereoselectivities (up to 99%), enantioselectivities (up to 98%) and yields (up to 91%) were observed. 


Keywords


Aldol reaction; Organocatalysis; Asymmetric synthesis; Prolinamide

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DOI: http://dx.doi.org/10.17344/acsi.2018.4748

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Copyright (c) 2020 Elif Keskin, Cigdem Yolacan, Feray Aydogan

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