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

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Keskin E., YOLAÇAN Ç., AYDOĞAN F.

ACTA CHIMICA SLOVENICA, vol.67, no.4, pp.1014-1023, 2020 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 67 Issue: 4
  • Publication Date: 2020
  • Doi Number: 10.17344/acsi.2018.4748
  • Journal Name: ACTA CHIMICA SLOVENICA
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Central & Eastern European Academic Source (CEEAS), Chemical Abstracts Core, EMBASE, MEDLINE, Directory of Open Access Journals, DIALNET
  • Page Numbers: pp.1014-1023
  • Yıldız Technical University Affiliated: Yes

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 0 degrees C in the presence of benzoic acid as co-catalyst. (S)-methyl-24(S)-3-hydroxy-2-((S)-3-pyrrolidine-2-carb oxamido)prop an amido) -3-phenylprop ano ate (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.