Issue 23, 2011
From the journal:

Chemical Communications

A one-pot, reductive amination/6-endo-trigcyclisation for the stereoselective synthesis of 6-substituted-4-oxopipecolic acids†

Lindsay S. Fowler,a   Lynne H. Thomas,a   David Ellisb  and  Andrew Sutherland*a  

* Corresponding authors

a WestCHEM, School of Chemistry, University of Glasgow, The Joseph Black Building, Glasgow, UK
E-mail: Andrew.Sutherland@glasgow.ac.uk
Fax: +44 141 330 4888
Tel: +44 141 330 5936

b Pfizer Ltd, Sandwich, Kent, UK

Abstract

The first stereoselective synthesis of 2,6-trans-6-substituted-4-oxo-L-pipecolic acids using a tandem reductive amination/6-endo-trigcyclisation process is described. The sequential reduction and cyclisation mediated by sodium cyanoborohydride allowed the preparation of a series of highly functionalised 6-alkyl and 6-aryl analogues.

Graphical abstract: A one-pot, reductive amination/6-endo-trigcyclisation for the stereoselective synthesis of 6-substituted-4-oxopipecolic acids

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C1CC11916H
Article type
Communication
Submitted
04 Apr 2011
Accepted
19 Apr 2011
First published
13 May 2011

Chem. Commun., 2011,47, 6569-6571

Permissions

Request permissions

A one-pot, reductive amination/6-endo-trigcyclisation for the stereoselective synthesis of 6-substituted-4-oxopipecolic acids

L. S. Fowler, L. H. Thomas, D. Ellis and A. Sutherland, Chem. Commun., 2011, 47, 6569 DOI: 10.1039/C1CC11916H

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