Optisch aktive 3‐Amino‐2H‐azirine als Bausteine für enantiomerenreine α,α‐disubstituierte α‐Aminosäuren: Synthese des α‐Methylphenylalanin‐Synthons and Einbau in Modell‐Peptide

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Abstract
Optically Active 3‐Amino‐2H‐azirines as Synthons for Enantiomerically Pure αα‐Disubstituted α‐Amino Acids: Synthesis of the α‐Methylphenylalanine Synthons and Some Model PeptidesThe synthesis of a novel 2‐benzyl‐2‐methyl‐3‐amino‐2H‐azirine derivative with a chiral amino group is described. Chromatographic separation of the diastereoisomer mixture yielded the pure diastereoisomers 9a and 9b (Scheme 4) which are the D‐ and L‐2‐methylphenylalanine ((α‐Me)Phe) synthons, respectively. The reaction of 9a and 9b with thiobenzoic acid and with Z‐leucine yielded the monothiodiamides 10a and 10b (Scheme 5) and the dipeptide derivatives 11a and 11b (Scheme 6), respectively. Methanolysis of 11b yielded 12b. The absolute configuration of 10a was established by X‐ray crystallography. The absolute configuration of (α‐Me)Phe in 12b has been deduced from the known configuration of L‐leucine.

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