Issue 12, 2003
From the journal:

Chemical Communications

Reactivity of 2-acylaminoacrylates with ketene diethyl acetal; [2 + 2] cycloadditions vs. tandem condensations†

Alberto Avenoza,*a   Jesús H. Busto,a   Noelia Canala  and  Jesús M. Peregrina*a  

* Corresponding authors

a Departamento de Química, Universidad de La Rioja, UA-CSIC, 26006 Logroño, Spain
E-mail: alberto.avenoza@dq.unirioja.es
Fax: +34 941 299655
Tel: +34 941 299655

Abstract

The reactivity of 2-acylaminoacrylates with ketene diethyl acetal can be modulated by means of thermal conditions to yield cyclobutanes for the preparation of protected β-hydroxycyclobutane-α-amino acids, or catalytic conditions that yield cyclohexanes by tandem condensations to obtain interesting building blocks that are alternatives to Danishefsky's diene.

Graphical abstract: Reactivity of 2-acylaminoacrylates with ketene diethyl acetal; [2 + 2] cycloadditions vs. tandem condensations

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Article information

DOI
https://doi.org/10.1039/B302000B
Article type
Communication
Submitted
20 Feb 2003
Accepted
22 Apr 2003
First published
13 May 2003

Chem. Commun., 2003, 1376-1377

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Reactivity of 2-acylaminoacrylates with ketene diethyl acetal; [2 + 2] cycloadditions vs. tandem condensations

A. Avenoza, J. H. Busto, N. Canal and J. M. Peregrina, Chem. Commun., 2003, 1376 DOI: 10.1039/B302000B

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