Organocatalytic Approach to (S)-1-Arylpropan-2-ols: Enantioselective Synthesis of the Key Intermediate of Antiepileptic Agent (−)-Talampanel

Abstract

An efficient organocatalytic route for the preparation of enantioselective synthesis of (S)-1-arylpropan-2-ols derivatives, including the key intermediate of antiepileptic agent (−)-talampanel is described. The key steps involved are L-proline-catalyzed asymmetric α-aminooxylation of aldehydes and regioselective tosylation of diols followed by reduction.

Keywords:

• Asymmetric α-aminooxylation
• enantioselective synthesis
• L-proline
• organocatalysis
• (S)-1-arylpropan-2-ols

ACKNOWLEDGMENTS

R. T. S. thanks the Council of Scientific and Industrial Research (CSIR), New Delhi, for a senior research fellowship. The authors are thankful to the Shimadzu Analytical Centre of the Department of Chemistry, University of Pune, for spectral analysis.

Notes

^a ee determined from the specific rotation value (see Refs. 17 and 18).

^b ee determined by chiral HPLC analysis.