John obtained his MSci degree in Chemistry in 2003 from the University of Bristol. He then remained at Bristol to study for my PhD degree (2007) under the guidance of Professor Timothy Gallagher. During this time his research focused on the development of cyclic sulfamidate based N-heterocyclic methodologies and their application to natural product synthesis. His first postdoctoral appointment (2007-2008) was with Professor Michael Krische at the University of Texas at Austin where he investigated transfer hydrogenative strategies for carbonyl addition. He then undertook a second postdoctoral appointment with Professor Timothy Donohoe at the University of Oxford where he focussed on the use of olefin cross metathesis for heteroaryl synthesis.
In 2010, he was awarded a Royal Society University Research Fellowship and commenced his independent career at the University of Bristol. His group’s research interests lie broadly within the area of asymmetric catalysis, with an emphasis on the development of green processes (atom economy, step economy and selectivity). Current studies are directed towards (i) the development of new methodology for heterocyclic chemistry, (ii) the application of these processes to natural product synthesis and (iii) the evaluation of natural product analogues for medicinal purposes. The understanding of reaction mechanism to increase the efficiency, scope and applicability of new transformations is also of paramount interest. John has been the recipient of a number awards and fellowships, including the RSC Harrison-Meldola Memorial Prize (2013), an ERC Starter Grant (2015), and the RSC Hickinbottom Award (2015).
Catalytic Chirality Generation: New Strategies for Heterocyclic Chemistry
Our research programme is focussed upon the development of new catalysis platforms that enable direct access to medicinally valuable chiral scaffolds. Recently, we outlined a metal-catalysed (3+1+2) carbonylative cycloaddition strategy for the synthesis of complex nitrogen containing scaffolds (Scheme 1A).1 The key metallacyclic intermediates 1 are generated by Rh-catalysed carbonylative ring expansion of readily available amino-substituted cyclopropanes. To control the regioselectivity of this process we have developed a directing group based strategy, which takes advantage of the N-protecting group (Scheme 1B). This approach controls (a) the regioselectivity of oxidative addition (into the more hindered cyclopropane C-C bond) and (b) the regioselectivity of CO insertion. Mechanistic aspects of this process will be discussed and prototypical catalytic processes that involve trapping of the metallacyclic intermediate with tethered alkynes or alkenes will be presented.