Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 1997; 1997(3): 322-324
DOI: 10.1055/s-1997-768
DOI: 10.1055/s-1997-768
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.
Chirality Transfer from Nitrogen to Carbon in the [2,3]-Meisenheimer Rearrangement
Further Information
Publication History
Publication Date:
31 December 2000 (online)
![](https://www.thieme-connect.de/media/synlett/199703/lookinside/thumbnails/10.1055-s-1997-768-1.jpg)
Oxidation of chiral, camphidin-based allylic tertiary amines gives rise to chiral tertiary amine-N-oxides, which undergo the [2,3]-Meisenheimer rearrangement with high levels of stereoselectivity. Reductive N,O-bond cleavage of the O-allyl-hydroxylamine gives access to the allylic alcohol unit.
Meisenheimer rearrangement - amine-N-oxide - allylic alcohol - camphidin auxiliary - chirality transfer