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Synlett 1998; 1998(5): 457-466
DOI: 10.1055/s-1998-1686
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Recent Developments in the Use of N-Phthaloyl-Amino Acid Derivatives in Synthesis

Christopher J. Easton* , Craig A. Hutton
  • *Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia; Fax 61-2-62 49 07 50; E-mail: easton@rsc.anu.edu.au
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Publication History

Publication Date:
31 December 2000 (online)

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Photolysis and free radical bromination of N-phthaloyl-amino acid derivatives each results in side chain functionalisation. Products of these reactions enable the synthesis of a wide range of functionalised amino acid derivatives in which the absolute stereochemistry is predetermined by that of the original amino acids and the relative stereochemistry is governed by the mechanisms of the reactions of those species. The utility of the methodology in asymmetric synthesis has been extended through the temporary introduction of a new stereochemical centre onto the phthaloyl group, for self-reproduction of chirality, while novel neighbouring group effects result in stereoconvergent syntheses in some cases.

amino acids - phthaloyl group - free radicals - β-hydroxyphenylalanine - stereocontrol

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