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

Abstract

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 s OH 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 H 3 PO 4 to produce racemic O 3 ‐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.