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One-Carbon Homologation of Knoevenagel Adducts: Enantioselective Access to Benzhydryl Derivatives

Janssens, Julien;De Roose, Madeline;Jacquemin, Alexis;Vanhosmael, Thomas;Robiette, Raphaël;et.al.
(2024) The Journal of Organic Chemistry — Vol. 89, n° 10, p. 7270-7274 (2024)

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Abstract
A one-carbon homologation of Knoevenagel adducts enabling the insertion of a CHAr fragment is reported. The strategy involves a sulfur ylide mediated cyclopropanation followed by the rearrangement of cyclopropanes and enables the synthesis of a series of benzhydryl derivatives. Mechanistic studies reveal that the cyclopropane rearrangement involves a Lewis acid catalyzed ring-opening followed by the 1,2-migration of an aryl group. The possibility of controlling the absolute stereochemistry of the generated stereogenic allylic carbon center using a chiral sulfonium ylide is demonstrated.
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Janssens, J., De Roose, M., Jacquemin, A., Vanhosmael, T., Delbrassinne, A., Collard, L., & Robiette, R. (2024). One-Carbon Homologation of Knoevenagel Adducts: Enantioselective Access to Benzhydryl Derivatives. The Journal of Organic Chemistry, 89(10), 7270-7274. https://doi.org/10.1021/acs.joc.4c00057 (Original work published 2024)