Metal-Free Deoxygenation of Chiral Nitroalkanes : An Easy Entry to α-Substituted Enantiomerically Enriched Nitriles
Articolo
Data di Pubblicazione:
2021
Citazione:
Metal-Free Deoxygenation of Chiral Nitroalkanes : An Easy Entry to α-Substituted Enantiomerically Enriched Nitriles / M. Pirola, C. Faverio, M. Orlandi, M. Benaglia. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 27:40(2021), pp. 10247-10250. [10.1002/chem.202100889]
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).
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
chiral nitriles, metal-free reactions; nitroalkanes; stereoselectivity; trichlorosilane
Elenco autori:
M. Pirola, C. Faverio, M. Orlandi, M. Benaglia
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