The Lloyd-Jones Research Group

Investigations into the Existence of Asymmetric Ion-pairing
in Pd-catalysed Allylic Alkylation

We have recently developed a novel method for following the path of both enantiomers of a racemic substrate through a Pd-catalysed allylic alkylation. We are now using the method to study the report of Trost and Bunt that there is significant asymmetric ion-pairing, in certain situations, in Pd-catalysed allylic alkylation - for example with the "Trost Modular ligand". Ion-pairing was offered as the explanation for the "memory effects" that can occur when cyclopenetenyl acetate and methyl carbonate are used as substrates.

References:

• "On the Question of the Symmetry of Formally Symmetrical p-(Allyl)palladium Cationic Intermediates in Allylic Alkylations", Barry M. Trost and Richard C. Bunt, J. Am. Chem. Soc., 118, 235-236, 1996.
• "Asymmetric "meso p-Allyls" in Pd-catalysed Allylic Alkylation: Stereochemical Labelling though Isotopic Desymmetrization", Guy C. Lloyd-Jones and Susanna C. Stephen, Manuscript in preparation 1998.

This project is being funded by a University of Bristol Scholarship 1996-1999.

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