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Teaching an Old Dog New Tricks?

A new catalytic strategy for aldol-type reactions
Figure from the paper

The aldol reaction is amongst the oldest and most established reactions in organic chemistry. However, despite being an intensive area of research, access to aldol products, β-hydroxy ketones, has been limited to the use of aldehydes and ketones. Using born catalysis the Thomas group have overcome this and allowed esters and lactones to be used to access aldol products.

Research in the Thomas group, driven by Adrián Moreno González as part of his Master’s project studies and Kieran Nicholson, has unearthed a new strategy for the synthesis of β-hydroxy ketones from esters and lactones (doi.org/10.1002/anie.202209584). This new methodology allows for the in situ synthesis of a nucleophilic enolate (from the enone) and an electrophilic aldehyde (from the ester) which can react together to give a β-hydroxy ketones. This catalytic strategy exploits the wide ranging reactivity of boron reagents and the use of transborylation as a method for main-group catalytic turnover. 

Significantly, this new reactivity provides chemists with a new retrosynthetic disconnection: the reaction of an enone and an ester to give β-hydroxy ketones.

This was great work from the group, particularly Adrián and Kieran. New disconnections in organic chemistry are not common, we are thrilled to share this simple approach to new reactivity.

Dr Stephen Thomas

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Tuesday, August 30, 2022