Nucleophilic Addition of Potassium O–Ethyl Dithiocarbonate to Baylis–Hillman Adducts Using 9–BBN as Catalyst

Ilsa Hernández–Ibinarriaga, 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 O–ethyl dithiocarbonate to Baylis–Hillman adducts in the presence of 9–BBN (9–borabicyclo[3.3.1]nonane) as a Lewis acid is reported. 9–BBN both protected the hydroxyl group and activated the carbonyl of the Michael acceptor.

Keywords: Xanthates; Baylis–Hillman adducts; 9–BBN as a Lewis acid.

Resumen

En este artículo se describe una adición de Michael diastereoselectiva del O–etilditiocarbonato de potasio comercial sobre aductos de Baylis–Hillman, utilizando 9–BBN (9–borabiciclo[3.3.1]no nano) como ácido de Lewis. El 9–BBN protegió el grupo hidroxilo y activó al mismo tiempo el grupo carbonilo del aceptor de Michael.

Keywords: Xantatos; aductos de Baylis–Hillman; 9–BBN, ácido de Lewis.

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Acknowledgements

Financial support from the DGAPA–UNAM (project PAPIIT–IN213407) 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 X–ray crystallography.

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