Nonsilyl bicyclic secondary amine catalyzed Michael addition of nitromethane to β,β-disubstituted α,β-unsaturated aldehydes

Kumar, RohtashRohtashKumarAvinash, AvinashAvinashAvinashMehta, RonakRonakMehtaAppayee, ChandrakumarChandrakumarAppayee2025-08-312025-08-312025-04-1410.1039/d5ob00277j2-s2.0-105003763824https://repository.iitgn.ac.in/handle/IITG2025/2818240244885The asymmetric Michael addition of nitroalkanes to β,β-disubstituted α,β-unsaturated aldehydes is a useful method for the construction of all-carbon quaternary stereocenters. Nonsilyl bicyclic secondary amine organocatalysts were employed in reactions involving a wide range of β,β-disubstituted α,β-unsaturated aldehydes with nitroalkanes to achieve products with all-carbon quaternary stereocenters in up to 69% yield and 95% ee. The scalability of this methodology was demonstrated at the 5.1 mmol scale. The synthetic utility of this methodology is showcased through the concise asymmetric synthesis of methsuximide, an anticonvulsant drug.en-USfalseNonsilyl bicyclic secondary amine catalyzed Michael addition of nitromethane to β,β-disubstituted α,β-unsaturated aldehydesArticlehttps://pubs.rsc.org/en/content/articlepdf/2025/ob/d5ob00277j4730-473414 April 202500WOS:001468873800001