An investigation of chiral diamides as organocatalysts in asymmetric aldol reaction

Yilmaz D. G., Aydoğan F., Yolaçan Ç.

JOURNAL OF HETEROCYCLIC CHEMISTRY, vol.59, no.7, pp.1169-1179, 2022 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 59 Issue: 7
  • Publication Date: 2022
  • Doi Number: 10.1002/jhet.4457
  • Journal Name: JOURNAL OF HETEROCYCLIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Aquatic Science & Fisheries Abstracts (ASFA), Chimica, EMBASE
  • Page Numbers: pp.1169-1179
  • Yıldız Technical University Affiliated: Yes

Abstract

Seven novel proline and 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (THIQA) based diamides were synthesized successfully by simple amidation reactions and characterized by their spectral data. Their catalytic activities in asymmetric aldol reaction were performed by the reactions of aliphatic ketones and various aromatic aldehydes. Especially, (S)-N-((S)-1-(morpholinoamino)-1-oxo-3-phenylpropan-2-yl)pyrrolidine-2-carboxamide (9e) showed good catalytic activities in water at room temperature in the presence of benzoic acid cocatalyst. The enantioselectivities were upto 89.6%, the diastereomeric ratios were upto 92/8, and yields were upto 97.3%. This catalyst showed its best catalytic activities in water; this is also an important contribution to green chemistry requirements.