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- Title
Metal‐Free Deoxygenation of Chiral Nitroalkanes: An Easy Entry to α‐Substituted Enantiomerically Enriched Nitriles.
- Authors
Pirola, Margherita; Faverio, Chiara; Orlandi, Manuel; Benaglia, Maurizio
- Abstract
A metal‐free, mild and chemodivergent transformation involving nitroalkanes has been developed. Under optimized reaction conditions, in the presence of trichlorosilane and a tertiary amine, aliphatic nitroalkanes were selectively converted into amines or nitriles. Furthermore, when chiral β‐substituted nitro compounds were reacted, the stereochemical integrity of the stereocenter was maintained and α‐functionalized nitriles were obtained with no loss of enantiomeric excess. The methodology was successfully applied to the synthesis of chiral β‐cyano esters, α‐aryl alkylnitriles, and TBS‐protected cyanohydrins, including direct precursors of four active pharmaceutical ingredients (ibuprofen, tembamide, aegeline and denopamine).
- Subjects
NITROALKANES; DEOXYGENATION; TRICHLOROSILANE; CYANOHYDRINS; TERTIARY amines; ESTERS
- Publication
Chemistry - A European Journal, 2021, Vol 27, Issue 40, p10247
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.202100889