American Chemical Society
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Crystallization Does It All: An Alternative Strategy for Stereoselective Aza-Henry Reaction

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journal contribution
posted on 2019-06-03, 16:06 authored by Michaela Marčeková, Peter Gerža, Michal Šoral, Ján Moncol, Dušan Berkeš, Andrej Kolarovič, Pavol Jakubec
An efficient and experimentally straightforward method for the stereoselective synthesis of a variety of β-nitro-α-amino carboxylic acids via aza-Henry (nitro-Mannich) reaction of aldimines is disclosed, yielding either anti- or a rarely reported syn-configuration. The reaction operates directly on free glyoxylic acid and generates imine species in situ. Crystallization-controlled diastereoselectivity enables isolation of the target compounds in high enantio- and diastereomeric purities by a simple filtration.