CHEMISTRY OF ALPHA-AMINONITRILES - AZIRIDINE-2-CARBONITRILE, A SOURCE OF RACEMIC O3-PHOSPHOSERINENITRILE AND GLYCOLALDEHYDE PHOSPHATE

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 TsOH 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. Copyright © 1990 Verlag GmbH & Co. KGaA, Weinheim