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Copper(II)-Catalyzed [2,3]-Sigmatropic Rearrangement ofN-Methyltetrahydropyridinium Ylids

Heath, Peter, Roberts, Edward, Sweeney, Joseph B., Wessel, Hans Peter and Workman, James A. (2003) Copper(II)-Catalyzed [2,3]-Sigmatropic Rearrangement ofN-Methyltetrahydropyridinium Ylids. The Journal of Organic Chemistry, 68 (10). pp. 4083-4086. ISSN 0022-3263
Abstract

A ring-contractive and highly diastereoselective [2,3]-sigmatropic rearrangement occurs when N-methyl-1,2,3,6-tetrahydropyridine is treated with sub-stoichiometric amounts of copper or rhodium salts, in the presence of ethyl diazoacetate, giving ethyl cis-N-methyl-3-ethenyl proline (4).

Information
URI:
https://eprints.hud.ac.uk/id/eprint/15277
URI:
https://eprints.hud.ac.uk/id/eprint/15277
Title:
Copper(II)-Catalyzed [2,3]-Sigmatropic Rearrangement ofN-Methyltetrahydropyridinium Ylids
Creators:
Heath, Peter, Roberts, Edward, Sweeney, Joseph B., Wessel, Hans Peter and Workman, James A.
Identification Number:
10.1021/jo034147v
Official URL:
http://dx.doi.org/10.1021/jo034147v
Date:
April 2003
Subjects:
Q Science > QD Chemistry
Schools:
School of Applied Sciences > Biomolecular Sciences Research Centre
Library
Item Type:
Article
Depositing User:
Joseph Sweeney
Date Deposited:
18 Oct 2012 10:46
Revision:
10
Last Modified:
28 Aug 2021 11:22
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