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Synlett 1998; 1998(6): 685-687
DOI: 10.1055/s-1998-1745
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Stereoselective Synthesis of Oxygenated Trisubstituted Olefins Using N-Ylides [2,3]Rearrangement

Kiyoshi Honda* , Daisuke Igarashi, Masatoshi Asami, Seiichi Inoue
  • *Department of Synthetic Chemistry, Faculty of Engineering, Yokohama National University, Tokiwadai, Hodogayaku, Yokohama 240, Japan; Fax + 81(45)3 39 39 70; E-mail: inoue@syn.synchem.bsk.ynu.ac.jp
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Publication Date:
31 December 2000 (online)

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[2,3]Sigmatropic rearrangement of N-(ethoxycarbonyl)-methyl-β-methallylammonium ylide with an oxygen functionality at the β-position or γ-position forms trisubstituted trans-olefins with high stereoselectivity. On the other hand, the rearrangement of salts having a tiglyl ester moiety of a carbethoxy group affords cis-olefins. The present method was applied to the synthesis of plaunotol.

trisubstituted (Z)-olefins - trisubstituted (E)-olefins - stereoselective synthesis - [2,3]sigmatropic rearrangement - ammonium ylide