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Synlett 2001; 2001(5): 0613-0616
DOI: 10.1055/s-2001-13389
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Alkylation of N′-[(S)-1′-Phenylethyl]-N-(diphenylmethylene)glycinamide using a Phase Transfer Catalyst (PTC) for Practical Asymmetric Syntheses of α-Amino Acid Derivatives

Hyun Ju Kim* , Sang-kuk Lee, Yong Sun Park
  • *Department of Chemistry, Konkuk University, Seoul 143-701, Korea; Fax + 822-3436-5382; E-mail: parkyong@kkucc.konkuk.ac.kr
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Publikationsdatum:
31. Dezember 2001 (online)

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The chiral auxiliary mediated stereoselective alkylation reaction of N′-[(S)-1′-phenylethyl]-N-(diphenylmethylene)glycinamide (1) using a phase transfer catalyst (PTC) is described. Alkylation of 1 using 18-crown-6 as a PTC for liquid-solid extraction of KOH in toluene gives best results. This methodology provides a practical protocol for the preparation of a variety of enantio-enriched unnatural α-amino acid derivatives up to 83 : 17 enantiomeric ratio.

phase transfer catalysis - asymmetric syntheses - alkylation - chiral auxiliaries - amino acids