Download PDF
Synlett 1999; 1999(9): 1465-1467
DOI: 10.1055/s-1999-2843
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.

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
Further Information

Publication History

Publication Date:
31 December 1999 (online)

  PDF Download  Permissions and Reprints All articles of this category

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

      >