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Metal‐Free Deoxygenation of Chiral Nitroalkanes: An Easy Entry to α‐Substituted Enantiomerically Enriched Nitriles
Author(s) -
Pirola Margherita,
Faverio Chiara,
Orlandi Manuel,
Benaglia Maurizio
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202100889
Subject(s) - deoxygenation , stereocenter , chemistry , trichlorosilane , organic chemistry , amine gas treating , aryl , enantiomeric excess , enantiomer , nitro , diastereomer , combinatorial chemistry , enantioselective synthesis , catalysis , alkyl , silicon
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).