N-Heterocyclic Carbene Catalyzed Asymmetric Hydration: Direct Synthesis of α-Protio and α-Deuterio α-Chloro and α-Fluoro Carboxylic Acids

Harit U. Vora and Tomislav Rovis*

*Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, Email: rovislamar.colostate.edu

H. U. Vora, T. Rovis, J. Am. Chem. Soc., 2010, 132, 2860-2861.

DOI: 10.1021/ja910281s

---

see article for more reactions

Abstract

Asymmetric hydration of α,α-dichloro aldehydes and α-halo enals via a NHC-catalyzed redox process gives enantioenriched α-chloro and α-fluoro carboxylic acids. The reaction allows the installation of an α-deuterium to give α-deutero α-halo acids using D₂O as the deuteron source.

see article for more examples

---

---

Key Words

α-chlorocarboxylic acids, carboxylic acids, organocatalysis

---

ID: J48-Y2010-0820