Nobel Prize in Chemistry 2026
Yesterday, the Nobel Prize in Chemistry was shared by Henri B. Kagan and Kenso Soai, for discovering non-linear effects in asymmetric catalysis and asymmetric autocatalysis. Until 1986, it was taken as fact that the ee of a product scales linearly with the ee of the chiral ligand. Kagan and co-workers showed the relationship between ligand chirality and product enantiomeric excess instead follows a positive non-linear effect. In the Sharpless epoxidation of geraniol with scalemic diethyl tartrate, the epoxide formed in higher ee than the linear rule allows, while a titanium-tartrate sulfide oxidation and the proline-catalysed Hajos-Parrish reaction fell below the line. Once two ligands sit on the metal, homochiral and heterochiral ML2 complexes coexist and can react at different rates. If the heterochiral complex is the slower one, the minor enantiomer is taken out of play, and stereochemical purity is amplified. Soai provided the most dramatic case. In 1990 he found that a pyridyl alkanol catalyses its own formation from pyridine-3-carbaldehyde and diisopropylzinc, though with erosion of ee. Five years later, with pyrimidine-5-carbaldehyde, the product overtook the catalyst: 5% ee became 55% in a single run and 90% after five. An alkynyl-substituted substrate later went from 0.00005% ee to above 99.5% in three runs, a 630,000-fold amplification. The Soai reaction can even deliver enantioenriched product from achiral starting materials alone, with the sense of chirality decided by statistical fluctuation. A plot of product ee against ligand ee is a cheap mechanistic probe for aggregates and higher-order catalysts, and a positive non-linear effect means the chiral input does not have to be enantiopure. Merck used this principle in the route to the leukotriene antagonist L-699,392, where a borane reagent made from alpha-pinene of 70% optical purity gave the alcohol in 95% ee. Asymmetric autocatalysis has reached antiviral chemistry too, in a process to a key intermediate of efavirenz, the FDA-approved antiretroviral used to treat HIV infection. Explore our range of building blocks for asymmetric catalysis at https://lnkd.in/eVbfw6Ua The original papers: Nonlinear effects in asymmetric synthesis. Examples in asymmetric oxidations and aldolization reactions https://lnkd.in/e7S2A\_FX Asymmetric autocatalysis and amplification of enantiomeric excess of a chiral molecule https://lnkd.in/eatJjYJA Amplification of Chirality from Extremely Low to Greater than 99.5% ee by Asymmetric Autocatalysis https://lnkd.in/eAWuzuAZ More information: https://lnkd.in/eN4-i9bJ
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