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Communication | Special issue | Vol 103, No. 1, 2021, pp.218-224
Published online, 29th October, 2020
DOI: 10.3987/COM-20-S(K)32
■ Hybrid Catalysis of 8-Quinolinecarboxaldehyde and Brønsted Acid for Efficient Racemization of α-Amino Amides and Its Application in Chemoenzymatic Dynamic Kinetic Resolution

Kohsuke Ohmatsu, Mari Kiyokawa, Yuto Shirai, Yuya Nagato, and Takashi Ooi*

*Institute of Transformative Bio-Molecules (WPI-ITbM), and Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University, Nagoya, 464-8601, Japan

Abstract

The combination of 8-quinolinecarboxaldehyde and benzoic acid proved to be an effective catalyst system for the racemization of N-unprotected α-aryl- or α-alkyl-substituted α-amino amides. Application of this system to chemoenzymatic dynamic kinetic resolution provided an efficient access to enantiomerically pure N-acetyl-α-amino amides in good to high yields.