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Short Paper | Special issue | Vol 101, No. 1, 2020, pp.299-311
Published online, 13th September, 2019
DOI: 10.3987/COM-19-S(F)4
Stereoselective Synthesis of β-Amino Acids by Aldol-Type Addition

David Benito-Garagorri, Wolfgang Felzmann, Sven Nerdinger, and Kathrin Höferl-Prantz*

*Global Portfolio, Sandoz GmbH, Biochemiestrasse 10, 6250 Kundl, Austria

Abstract

A synthesis of α-oxygenated β-amino acid derivatives using an aldol-type addition is described. Depending on the enol equivalent different oxidation states of the oxygen substituent are accessible, while choosing a chiral imine allows to generate the aldol product in a stereoselective manner. This methodology has been applied to the synthesis of the biologically active compound Telaprevir, used in the traetment of Hepatitis C.