Download PDF
Synlett 1994; 1994(9): 739-740
DOI: 10.1055/s-1994-22992
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.

Highly Stereoselective Synthesis of Trisubstituted (E)-Olefins Using the Base-Induced [3,3]Rearrangement of N-Substituted ß-Methallyldimethylammonium Salts in Protic Solvents

Kiyoshi Honda* , Seiichi Inoue
  • *Department of Synthetic Chemistry, Faculty of Engineering, Yokohama National University, Tokiwadai, Hodogayaku, Yokohama 240, Japan
Further Information

Publication History

Publication Date:
18 September 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

Treatment of allyl- and propynyl-ß-methallyldimethylammonium salts with alkoxide bases in protic solvents resulted in the formation of enammonium salts followed by spontaneous [3,3]sigmatropic rearrangement to give trisubstituted (E)-olefins possessing a formyl group with complete stereoselectivity.

      >