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Synlett 1998; 1998(6): 685-687
DOI: 10.1055/s-1998-1745
DOI: 10.1055/s-1998-1745
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 Oxygenated Trisubstituted Olefins Using N-Ylides [2,3]Rearrangement
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Publikationsverlauf
Publikationsdatum:
31. Dezember 2000 (online)
![](https://www.thieme-connect.de/media/synlett/199806/lookinside/thumbnails/10.1055-s-1998-1745-1.jpg)
[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