153225-89-9Relevant articles and documents
Metal-Free Deoxygenation of Chiral Nitroalkanes: An Easy Entry to α-Substituted Enantiomerically Enriched Nitriles
Pirola, Margherita,Faverio, Chiara,Orlandi, Manuel,Benaglia, Maurizio
supporting information, p. 10247 - 10250 (2021/06/18)
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).
Synthetic applications of optically active cyanohydrins. Enantioselective syntheses of the hydroxyamides tembamide and aegeline, the cardiac drug denopamine, and some analogues of the bronchodilator salbutamol
Brown, Roger F. C.,Donohue, Andrew C.,Roy Jackson,McCarthy, Tom D.
, p. 13739 - 13752 (2007/10/02)
The natural hydroxyamides, (-)-tembamide and (-)-aegeline, and the cardiac drug (-) -denopamine have been prepared in homochiral form in good overall yield (>65%) from para - methoxy or para-allyloxybenzaldehyde by synthetic sequences involving entantioselective hydrocyanation of the aldehydes. Similar chemistry has been used to prepare analogues of the bronchodilator (-)-salbutamol both in high yield and with good enantiomeric excess.
A Synthesis of (-)-Denopamine
Brown, Roger F. C.,Jackson, W. Roy,McCarthy, Tom D.
, p. 2149 - 2150 (2007/10/02)
The important cardiac drug, (-)-denopamine, has been synthesized in 68percent overall yield from para-allyloxybenzaldehyde via (R)-2-hydroxy-2-acetonitrile.
