NDLI: A Domino Aza-Prins/Friedel–Crafts Reaction for the Synthesis of Benzomorphans

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A Domino Aza-Prins/Friedel–Crafts Reaction for the Synthesis of Benzomorphans

Content Provider	Scilit
Author	Maison, Wolfgang Ploog, Jasper Pongs, Juliane Weber, Stefan
Copyright Year	2016
Description	A new domino sequence involving an aza-Prins cyclization and a Friedel–Crafts reaction is reported. The starting materials are N-tosylimines prepared in situ from N-tosylated homoallylamines and derivatives of phenylacetaldehyde. The domino reactions are mediated by Brønsted and Lewis acids and give benzoannelated azabicyclononanes. Many derivatives thereof contain the benzomorphan scaffold and are thus of pharmaceutical interest as analgesics. The method provides a one-step access to substituted benzomorphans from readily available starting materials. The yields are generally good and various substituents are tolerated.
Related Links	http://pdfs.semanticscholar.org/5f7d/c735683ba643652c30ca14e00bce0bb705e0.pdf http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0036-1588071.pdf
Ending Page	703
Page Count	11
Starting Page	693
ISSN	00397881
e-ISSN	1437210X
DOI	10.1055/s-0036-1588071
Journal	Synthesis
Issue Number	03
Volume Number	49
Language	English
Publisher	Georg Thieme Verlag KG
Publisher Date	2016-09-14
Access Restriction	Open
Subject Keyword	Journal: Synthesis Organic Chemistry Aza-prins Reaction Friedel–crafts Reaction Domino Reaction
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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