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

E Wagner, YB Xiang, K Baumann, J Gück…

Index: Wagner, Ernst; Xiang, Yi-Bin; Baumann, Karl; Gueck, Juergen; Eschennmoser, Albert Helvetica Chimica Acta, 1990 , vol. 73, # 5 p. 1391 - 1409

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Citation Number: 35

Abstract

Racemic aziridine-2-carbonitrile (ruc-1) in MeCN solution reacts regioselectively (> 90%) with 2 equiv. of TsOH at room temperature to form the hydrotosylate of racemic 03- tosylserinenitrile (ruc-2) via a B-ring opening (Scheme 2). A similar regioselective reaction takes place between rac-1 and H3P04 to produce racemic 03-phosphoserinenitrile (rac-3) which is in turn a source of glycolaldehyde phosphate (= formylmethyl ...