Diastereoselective Mannich Synthesis of β-Amino Ketones Catalyzed by a ZrO(L-Proline)2 Hybrid System
Letters in Organic Chemistry, 2026 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Basım Tarihi: 2026
- Doi Numarası: 10.2174/0115701786477661260826144235
- Dergi Adı: Letters in Organic Chemistry
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core
- Anahtar Kelimeler: diastereoselective synthesis, hybrid catalysis, L-proline, Mannich reaction, multicomponent reaction, zirconium catalyst, β-amino ketones
- Erciyes Üniversitesi Adresli: Evet
Özet
A three-component Mannich reaction catalyzed by a ZrO(L-proline)2 hybrid catalyst was investigated for the synthesis of β-amino ketones under mild conditions. Aromatic aldehydes, anilines, and cyclohexanone were reacted in the presence of the catalyst to afford the corresponding products in moderate yields (32-68%) with anti:syn ratios ranging from 78:22 to 100:0. Catalyst screening demonstrated that ZrO(L-proline)2 promoted improved diastereoselectivity compared with related zinc and zirconium salts. Solvent effects strongly influenced both yield and stereochemical outcome, with p-xylene affording complete anti-selectivity at lower conversion. Preliminary substrate scope studies confirmed the applicability of the catalytic system toward substituted aromatic aldehydes. The results suggest that cooperative Lewis acid/organic ligand activation may contribute to stereochemical control in the Mannich transformation.