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Research: Asymmetric Catalysis

We are engaged in the development of new catalysts for demanding asymmetric transformations. Our research in this area is showcased in two specific areas:

1. Plagiarizing Proteins: we have shown through our work in the area of foldamers that we can control hydrogen bonding to generate conformationally well-defined secondary structural elements. We aim to extend this work to use these materials as scaffolds for catalysts that exploit features common to enzyme catalyzed processes.

We aim to establish a structure-conformation-catalysis relationship, leading to the development of more efficient and more effective catalysts.

2. Electrocyclic Reactions: Pericyclic reactions are a class of transformations that comprise sigmatropic rearrangements, group transfer reactions, cycloadditions and electrocyclic reactions.  Since Woodward and Hoffman delineated a rationale for the mechanism and stereochemistry of these reactions they have become powerful synthetic tools. Whilst sigmatropic rearrangements and cycloadditions are cornerstones of contemporary synthetic methodology, many electrocyclic reactions are not fully exploited.  The high temperatures often required to initiate these transformations and difficulties associated in assembling precursors, coupled with limited opportunities for exerting stereocontrol often preclude their use in complex molecule synthesis; there are no general methods for the asymmetric catalysis of electrocyclic reactions. We are engaged in the development of methods for asymmetric catalysis of electrocyclic processes.

For relevant publications see:

"Plagiarizing proteins: enhancing efficiency in asymmetric hydrogen bonding catalysis
through positive cooperativity" Angew. Chem. Int. Ed., 2009, 48, pp. 7391-7394.

"An approach to catalytic asymmetric 6π electrocyclization:
asymmetric synthesis of functionalized indolines,
Angew. Chem. Int. Ed., 2009, in press. pdf

Foldamers -- Total Synthesis -- Catalysis