Nonsilyl bicyclic secondary amine catalyzed Michael addition of nitromethane to β,β-disubstituted α,β-unsaturated aldehydes
Year: 2025
Type: article
Abstract: The 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.
Source: Organic & Biomolecular Chemistry
DOI: 10.1039/d5ob00277j
Authors: Rohtash Kumar, Avinash Avinash, Ronak Mehta, Chandrakumar Appayee
Institution: Indian Institute of Technology Gandhinagar
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
OpenAlex ID: W4409428264