Preparation of α??Aminobenzylphosphonic Acids with a Stereogenic Quaternary Carbon Atom via Microscopically Configurationally Stable α??Aminobenzyllithiums

…, M Hanbauer, F Hammerschmidt

Index: Kuliszewska, Edyta; Hanbauer, Martin; Hammerschmidt, Friedrich Chemistry - A European Journal, 2008 , vol. 14, # 28 p. 8603 - 8614

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Citation Number: 25

Abstract

Abstract The enantiomers of 1-phenylethylamine were phosphorylated with diethyl chlorophosphate/Et 3 N and then Boc-protected (Boc= tert-butoxycarbonyl) at the nitrogen atom. These phosphoramidates were metalated by using sBuLi/N, N, N′, N′- tetramethylethylenediamine (TMEDA) to give α-aminobenzyllithiums that isomerised to α- aminophosphonates in yields of up to 80% with retention of the configuration at the carbon ...