Synthesis of Chiral NADH Analog Based on Proline Template Including Thiourea and Nicotinic Acid Moieties

Abstract

Chiral reductase-mimicking organic molecule built on proline template incorporating a covalently bound NADH mimic via thiourea, and related reducing agent Hantzsch dihydropyridine, was designed. A synthetic path was developed involving interlinking of chiral proline derivatives with thiourea and subsequent coupling reaction with nicotinoyl chloride. The structure of target compound was studied by x–ray, indicating a double H bond with thiourea hydrogens and oxygen O1 of benzylcarbamate fragment. The reduction of benzil and imines was performed.

Keywords:

• Enantioselective synthesis
• NADH analog
• proline
• reduction

ACKNOWLEDGMENT

This work was supported by Nordforsk via the Nordic-Baltic Network in Crystal Engineering and Supramolecular Materials.