UK scientists have developed a scalable, resolution-free synthesis of a helical DMAP organocatalyst.
In 2011 Dave Carbery (University of Bath) and colleagues made a helicene catalyst that they say was the most active chiral DMAP-like nucleophilic catalyst (DMAP = 4-dimethylamino pyridine). It was an effective catalyst for the acylative kinetic resolution of chiral secondary alcohols. With it, the team achieved reactions on a gram scale using only 1mg of catalyst – a 0.05mol% loading. However, the catalyst needed HPLC resolution.
They are now able to make more than 1g of the helical DMAP without any resolution. They say that it is also possible to do late-stage functionalisation.
Link to journal article
Point-to-helical chirality transfer for a scalable and resolution-free synthesis of a helicenoidal DMAP organocatalyst
M R Crittall, N W G Fairhurst and D R Carbery
Chem. Commun., 2012, DOI: 10.1039/c2cc35583c
