Preparation of alpha-aminobenzylphosphonic acids with a stereogenic quaternary carbon atom via microscopically configurationally stable alpha-aminobenzyllithiums.

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 alpha-aminobenzyllithiums that isomerised to alpha-aminophosphonates in yields of up to… (More)
DOI: 10.1002/chem.200800475

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