Asymmetric Mannich Reaction of α-(2-Nitrophenylsulfenyl)imino Acetamide: A Cyclization-Driven Process
Abstract
An enantioselective Mannich reaction of 2-(2-nitrophenylsulfenylimino)acetamide is described. Under the optimized conditions using proline, triethylamine, and diarylthiourea additives, the initially formed Mannich adduct undergoes irreversible cyclization to afford cyclic hemiaminal products in 21-58% yield, with diastereomeric ratios ranging from 53:47 to 83:17. Enantioselectivity reaches up to 97% ee. The presence of N-H functionality of the substrate is crucial for this cyclization; in its absence, the Mannich adduct undergoes facile decomposition. Subsequent reduction in this intermediate efficiently furnished the corresponding homoserine derivative.
Fields of Study & Subjects
Synthesis and Catalytic Reactions
Asymmetric Synthesis and Catalysis
Synthesis and pharmacology of benzodiazepine derivatives
Publication details
- Journal / source
- Molecules
- Publisher
- MDPI AG
- Volume
- 31
- Issue
- 3
- Pages
- 449–449
- Publication date
- 27 January 2026
- Language
- EN