Chemie von α-Aminonitrilen. Aziridin-2-carbonitril,ein Vorläufer von rca-O3-Phosphoserinnitril und Glycolaldehyd-phosphat

Chemistry of α-Aminonitriles. Aziridine-2-carbonitrile, a Source of Racemic O′-Phosphoserinenitrile and Glycolaldehyde Phosphate Racemic aziridine-2-carbonitrile (rac- 1 ) in MeCN solution reacts regioselectively (> 90%) with 2 equiv. of T_sOH at room temperature to form the hydrotosylate of racemic O3-tosylserinenitrile (rac- 2 ) via β-ring opening (Scheme 2). A similar regioselective reaction takes place between rac-l and H₃PO₄ to produce racemic O₃-phosphoserinenitrite (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. The English Footnotes (*) referring to Schemes 1-7 are intended to provide an extension of this summary.