Download PDF
Synlett 2001; 2001(5): 0613-0616
DOI: 10.1055/s-2001-13389
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
31 December 2001 (online)

  PDF Download  Permissions and Reprints All articles of this category

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