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Journal of the Mexican Chemical Society
versión impresa ISSN 1870-249X
J. Mex. Chem. Soc vol.53 no.2 Ciudad de México abr./jun. 2009
Article
Nucleophilic Addition of Potassium OEthyl Dithiocarbonate to BaylisHillman Adducts Using 9BBN as Catalyst
Ilsa HernándezIbinarriaga, and Luis D. Miranda*
Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México, D.F. 04510, México. *Responsible author.
Received May 11, 2009
Accepted June 26, 2009
Abstract
An efficient diastereoselective Michael addition of the commercial potassium Oethyl dithiocarbonate to BaylisHillman adducts in the presence of 9BBN (9borabicyclo[3.3.1]nonane) as a Lewis acid is reported. 9BBN both protected the hydroxyl group and activated the carbonyl of the Michael acceptor.
Keywords: Xanthates; BaylisHillman adducts; 9BBN as a Lewis acid.
Resumen
En este artículo se describe una adición de Michael diastereoselectiva del Oetilditiocarbonato de potasio comercial sobre aductos de BaylisHillman, utilizando 9BBN (9borabiciclo[3.3.1]no nano) como ácido de Lewis. El 9BBN protegió el grupo hidroxilo y activó al mismo tiempo el grupo carbonilo del aceptor de Michael.
Keywords: Xantatos; aductos de BaylisHillman; 9BBN, ácido de Lewis.
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Acknowledgements
Financial support from the DGAPAUNAM (project PAPIITIN213407) is gratefully acknowledged and Dr. Joseph M. Muchowski for many helpful discussions. Also we thank H. Rios, R. Patiño, J. Pérez, L. Velasco, N. Zavala, E. Hernández, M. I. Chávez and A. Peña for technical support and R. A. Toscano and S. Hernández for Xray crystallography.
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