Chemistry of α-Aminonitriles. Aziridin-2-carbonitrile, a Source of Racemic O3-Phosphonoserinenitrile and Glycolaldehyde Phosphate

Article abstract of DOI:10.1002/hlca.19900730525

Racemic aziridine-2-carbonitrile (rac-1) in MeCN solution reacts regioselectively (>90percent) with 2 equiv. of TsOH at room temperature to form the hydrotosylate of racemic O³-tosylserinenitrile (rac-2) via a β-ring opening (Scheme 2).A similar regioselective reaction takes place between rac-1 and H3PO4 to produce racemic O³-phosphoserinenitrile (rac-3) which is in turn a source of glycolaldehyde phosphate (=formylmethyl dihydrogenphosphate) under the conditions of a 'retro-Strecker' reaction in aqueous solution (Scheme 6).These experiments document a close structural relationship between the simplest of the sugar phosphates and an α-aminonitrile precursor.