Organocatalytic Nobels

Organocatalytic Nobels
06 October 2021 - Prizes

The Nobel Prize this year has been awarded to Benjamin List and David MacMillan for their work in asymmetric organocatalysis. List has been a contender for years and years, his name appears in the annual Nobel predictions on this blog as early as 2009.

In 2000 List, Lerner and Barbas published an article on the intermolecular reaction between acetone and 4-nitrobenzaldehyde to the aldol adduct catalysed by L-proline for which they proposed an enamine intermediate (DOI). The reaction has a precedent in the Hajos–Parrish–Eder–Sauer–Wiechert reaction developed in industry in the 1970s, which is the intramolecular version. The Nobel people acknowledge this work but also argue that Hajos et al. quickly abandoned the research and also that they backed the wrong reaction mechanism. Zoltan Hajos would turn in his grave if he wasn’t still very much alive at 95. Years ago I contributed to the Hajos-Parrish reaction page on Wikipedia for some time and Zoltan himself was a fellow editor although he was not one to work according to the editorial guidelines. In his writings he bemoaned de decision by no-one other than Benjamin List in 2002 to add the three additional names to the Hajos-Parrish reaction when he was no doubt comfortable with the existing one.

The reaction mechanism has been hotly debated for some time. For example in 2007 Seebach and Eschenmoser (two very well-known chemistry tycoons) took 46 pages to describe an entirely different one and also a wrong one. List has more than one mention in this blog (fanzine?), we have a weird catalyst here , a organocatalysis update here and domino's here

Also in 2000 and also in the same journal (JACS) Jen, Wiener and MacMillan published their work on imidazolidinone organocatalysis (doi). MacMillan went on to invent a lot of other things and also has several mentions in this blog with asymmetric ylides here, SOMO catalysis here , deaminations here and high throughput synthesis here.