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Synlett 1999; 1999(9): 1465-1467
DOI: 10.1055/s-1999-2843
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Stereoselective Synthesis of Novel Chimerical Amino Acids via a Photochemical Key Step

Pablo Wessig*
  • *Institut für Chemie, Humboldt-Universität zu Berlin, Hessische Str. 1-2, D-10115 Berlin, Germany; Fax + 49(30)20 93 69 40; E-mail: pablo.wessig@chemie.hu-berlin.de
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Publication Date:
31 December 1999 (online)

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The synthesis of novel chimerical amino acid derivatives 6-8 bearing the 6-azatricyclo[3.3.1.03,7]nonane (methanotropane)skeleton is described. Starting with one chirality centre in L-4-oxoprolines 2 we succeeded in the fully stereoselective introduction of four new chirality centres. The key step of our synthetic route is a photochemical cyclization of phenyl ketones, whose stereoselectivity has been explained by the different stability of the triplet biradical conformers.

amino acid - stereoselective synthesis - cyclizations - photochemistry - radical reactions