Issue 36, 2007
From the journal:

Chemical Communications

Mild lanthanide(iii) catalyzed formation of 4,5-diaminocyclopent-2-enones from 2-furaldehyde and secondary amines: a domino condensation/ring-opening/electrocyclization process†‡

Sze-Wan Lia  and  Robert A. Batey*a  

* Corresponding authors

a Department of Chemistry, 80 St. George Street, University of Toronto, Toronto, Ontario, Canada
E-mail: rbatey@chem.utoronto.ca
Fax: +1(416) 978-5059
Tel: +1(416) 978-5059

Abstract

Lewis acid catalyzed reaction of 2-furaldehyde and secondary amines results in the formation of 4,5-diaminocyclopent-2-enones exclusively as the trans diastereomers: computational studies support the stereochemistry of the adducts as arising from a thermal conrotatory π4a electrocyclization of an initial ring-opened intermediate (a deprotonated Stenhouse salt).

Graphical abstract: Mild lanthanide(iii) catalyzed formation of 4,5-diaminocyclopent-2-enones from 2-furaldehyde and secondary amines: a domino condensation/ring-opening/electrocyclization process

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Article information

DOI
https://doi.org/10.1039/B709337N
Article type
Communication
Submitted
23 May 2007
Accepted
14 Jun 2007
First published
09 Jul 2007

Chem. Commun., 2007, 3759-3761

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Mild lanthanide(III) catalyzed formation of 4,5-diaminocyclopent-2-enones from 2-furaldehyde and secondary amines: a domino condensation/ring-opening/electrocyclization process

S. Li and R. A. Batey, Chem. Commun., 2007, 3759 DOI: 10.1039/B709337N

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