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Synlett 1994; 1994(9): 739-740
DOI: 10.1055/s-1994-22992
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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
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Publication Date:
18 September 2002 (online)

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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.