PDF herunterladen
Synlett 2001; 2001(10): 1506-1510
DOI: 10.1055/s-2001-17475
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.

Synthesis of 1-Azaspirocycles via Lewis Acid-Mediated Spirocyclization of Cyclic N-Acyl-N,O-acetals

Toshimasa Ito* , Naoki Yamazaki, Chihiro Kibayashi
  • *School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan; Fax + 81-426-76-4475; E-mail: kibayashi@ps.toyaku.ac.jp
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
27. September 2001 (online)

 als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik
Preview

A new approach to 1-azaspirocycles has been developed starting from cyclic N-acyl-N,O-acetals. This sequence involves olefin-iminium cyclization mediated by Lewis acids leading to the spirocyclization products including the chlorinated products and the olefinic products. Mixtures of these products underwent catalytic hydrogenation and reductive dechlorination to produce the 1-azaspirans.

N-acyl-N,O-acetals - Lewis acid - iminium ions - spirocyclization - 1-azaspirocycles