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Palladium catalysed asymmetric alkylation of benzophenone Schiff base glycine esters in ionic liquids

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Abstract

Asymmetric alkyl substitution of various benzophenone Schiff base substrates under biphasic conditions proceeded using optically active Palladium(II) complexes. The corresponding products were obtained in high yields but with moderate enantiomeric excess (ee). Addition of specific ionic liquids to the reaction medium enhanced reactivity and selectivity for phase transfer catalytic (PTC) glycine alkylation. It has been found that there is an anionic influence of the ionic liquids that modify the steric environment around the enolate ion. A computer-assisted molecular design of enantioselective phase-transfer catalysis with the palladium complex and the ionic liquid has been done.

Combination of an asymmetric palladium catalyst and a prochiral ionic solvent promotes glycine alkylation under mild conditions.

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Authors and Affiliations

  1. Department of Chemistry and Research institute for Basic Sciences, Kyung Hee University, 1 Hoegi-Dong, Dongdaemun-Gu, Seoul 130-701, Republic of Korea

    DAE HYUN KIM, JIN KYU IM, DAE WON KIM, MINSERK CHEONG & HOON SIK KIM

  2. Department of Chemistry, Ramsaday College, Amta, Howrah 711401, India

    DEB KUMAR MUKHERJEE

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  1. DAE HYUN KIM
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Correspondence to HOON SIK KIM.

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KIM, D.H., IM, J.K., KIM, D.W. et al. Palladium catalysed asymmetric alkylation of benzophenone Schiff base glycine esters in ionic liquids. J Chem Sci 123, 467–476 (2011). https://doi.org/10.1007/s12039-011-0093-4

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