Issue 5, 2010
From the journal:

Organic & Biomolecular Chemistry

A detailed investigation of the aza-Prins reaction†

Adrian P. Dobbs,*ab   Sebastien J. J. Guesné,b   Robert J. Parker,b   John Skidmore,c   Richard A. Stephensond  and  Mike B. Hursthoused  

* Corresponding authors

a School of Biological and Chemical Sciences, Joseph Priestley Building, Queen Mary University of London, Mile End Road, London, United Kingdom
E-mail: A.Dobbs@qmul.ac.uk

b School of Chemistry, University of Exeter, Stocker Road, Exeter, United Kingdom

c Neurosciences Centre of Excellence for Drug Discovery, GlaxoSmithKline, New Frontiers Science Park, Third Avenue, Harlow, Essex, United Kingdom

d EPSRC National Crystallographic Service, Chemistry, University of Southampton, Southampton, United Kingdom

Abstract

The development of a Lewis acid-promoted aza-Prins reaction to form piperidines and pyrrolidines is described. Indium trichloride has been found to be a highly successful and mild Lewis acid for promoting this reaction. A thorough mechanistic investigation is described, including the factors that influence the formation of the 5- or 6-membered ring product(s).

Graphical abstract: A detailed investigation of the aza-Prins reaction

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/B915797B
Article type
Paper
Submitted
03 Aug 2009
Accepted
31 Oct 2009
First published
05 Jan 2010

Org. Biomol. Chem., 2010,8, 1064-1080

Permissions

Request permissions

A detailed investigation of the aza-Prins reaction

A. P. Dobbs, S. J. J. Guesné, R. J. Parker, J. Skidmore, R. A. Stephenson and M. B. Hursthouse, Org. Biomol. Chem., 2010, 8, 1064 DOI: 10.1039/B915797B

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements