Article

 

N-N Torsion Angle in BINAM-Mono and Bis(Sulfonamide) Ligands and its Effect on the Catalytic Asymmetric Transfer Hydrogenation (ATH) of Aromatic Ketones

 

Angélica Barrón-Jaime,¹ Gerardo Aguirre,¹ Miguel Parra-Hake,¹ Daniel Chávez,¹ Domingo Madrigal,¹'² Belynda Sanders,² Andrew L. Cooksy² and Ratnasamy Somanathan¹*

 

¹ Centro de Graduados e Investigación, Instituto Tecnológico de Tijuana, Apartado Postal 1166, 22000 Tijuana, B. C., México.

² Department of Chemistry, San Diego State University, San Diego, CA 92182-1030, USA. *Corresponding author: somanatha@sundown.sdsu.edu.

 

Received June 14, 2010.
Accepted October 28, 2010.

 

Resumen

Los ligandos L1 y L2 se sintetizaron a partir de (R)-(+)-1,1'-binaftil-2,2'-diamina comercialmente disponible y se probaron con Rh^IIICp* como catalizadores en la reducción asimétrica por transferencia de hidrógeno de cetonas aromáticas en formiato de sodio acuoso como la fuente de hidruro. Los resultados fueron comparados con los de los ligandos derivados de 1,2-, 1,4-, y 1,6-diaminas, y correlacionados con el tamaño del anillo quelato metal-ligando y los ángulos de torsión N-N determinados por cálculos teóricos.

Palabras clave: Transferencia de hidrógeno asimétrica, ligandos monosulfonamida, complejos Rh^IIICp*, medio acuoso.

 

Abstract

Ligands L1 and L2 were synthesized from commercially available (R)-(+)-1,1'-binaphthyl-2,2'-diamine and tested with Rh^IIICp* as catalysts in the asymmetric transfer hydrogenation of aromatic ketones in aqueous sodium formate. The results were compared with ligands derived from 1,2-, 1,4-, and 1,6-diamines, and correlated to the metal chelate ring size and the N-N torsion angles determined by theoretical calculations.

Keywords: Asymmetric transfer hydrogenation, monosulfonamide ligands, Rh^IHCp* complexes, aqueous media.

 

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Acknowledgements

Support for this work from Consejo Nacional de Ciencia y Tecnología (CONACyT) Grant 60475 and Dirección General de Educación Superior Tecnológica (DGEST) Grant 944.08P is gratefully acknowledged. A. Barrón-Jaime and D. Madrigal thank CONACyT for graduate scholarship and sabbatical fellowship, respectively. B. Sanders thanks the NIH for fellowship support (NIW). A. L. Cooksy thanks the NSF for partial support (CHE-0719575).

 

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