Issue 5, 2002
From the journal:

Chemical Communications

Asymmetric Michael addition of formaldehyde N,N-dialkylhydrazones to alkylidene malonates

Juan Vázquez,a   Auxiliadora Prieto,a   Rosario Fernández,a   Dieter Endersb  and  José M. Lassaletta*c  

* Corresponding authors

a Departamento de Química Orgánica, Universidad de Sevilla, Apdo de Correos No. 553, Seville, Spain

b Institut für Organische Chemie, RWTH-Aachen, Professor Pirlet Strasse, 1, Aachen, Germany

c Instituto de Investigaciones Químicas, c/ Americo Vespuccio s/n, Seville, Spain
E-mail: jmlassa@cica.es

Abstract

Enantiopure formaldehyde N,N-dialkylhydrazones 1 smoothly react with prochiral alkylidene malonates 2 in the presence of MgI2 to afford the corresponding Michael adducts 3 in excellent yields and good diastereoselectivities; direct racemization-free BF3·OEt2-catalyzed thiolysis of the hydrazone C[double bond, length as m-dash]N bond affords the corresponding dithioketals 7 in optically pure or enantiomerically enriched form.

Graphical abstract: Asymmetric Michael addition of formaldehyde N,N-dialkylhydrazones to alkylidene malonates

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Article information

DOI
https://doi.org/10.1039/B200209B
Article type
Communication
Submitted
04 Jan 2002
Accepted
24 Jan 2002
First published
11 Feb 2002

Chem. Commun., 2002, 498-499

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Asymmetric Michael addition of formaldehyde N,N-dialkylhydrazones to alkylidene malonates

J. Vázquez, A. Prieto, R. Fernández, D. Enders and J. M. Lassaletta, Chem. Commun., 2002, 498 DOI: 10.1039/B200209B

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