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Ernst Wagner Yi-Bin Xiang Karl Baumann Jürgen Gück Albert Eschenmoser 《Helvetica chimica acta》1990,73(5):1391-1409
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. 相似文献
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