RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000083.xml
Synlett 1998; 1998(12): 1429-1431
DOI: 10.1055/s-1998-1978
DOI: 10.1055/s-1998-1978
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.
Enantioselective [2,3]-Wittig Rearrangement via Sparteine-Mediated Lateral Metalation of N,N-Dialkyl-o-allyloxymethylbenzamides and o-Substituted Benzyl Prenyl Ethers
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
31. Dezember 2000 (online)
![](https://www.thieme-connect.de/media/synlett/199812/lookinside/thumbnails/10.1055-s-1998-1978-1.jpg)
The (-)-sparteine-mediated enantioselective [2,3]-Wittig rearrangement of N,N-dialkyl-o-allyloxymethylbenzamides and o-substituted benzyl prenyl ethers has been investigated. With N,N-diethyl-o-allyloxymethylbenzamide, enantiomeric excess up to 60% was observed in pentane. These results suggest that the carbamoyl group can effectively assist the transfer of stereoinformation by coordinating with the (-)-sparteine-n-BuLi complex. Other functional groups (OMe, OCONR2, OMOM, F) were impotent to the enantiodifferentiation of this rearrangement.
[2,3]-Wittig rearrangement - (-)-sparteine - benzyl prenyl ether - lateral metalation