272109-12-3Relevant articles and documents
A Modular and Diastereoselective 5 + 1 Cyclization Approach to N-(Hetero)Aryl Piperidines
Larsen, Matthew A.,Hennessy, Elisabeth T.,Deem, Madeleine C.,Lam, Yu-Hong,Saurí, Josep,Sather, Aaron C.
supporting information, p. 726 - 732 (2020/01/31)
A new general de novo synthesis of pharmaceutically important N-(hetero)aryl piperidines is reported. This protocol uses a robustly diastereoselective reductive amination/aza-Michael reaction sequence to achieve rapid construction of complex polysubstituted ring systems starting from widely available heterocyclic amine nucleophiles and carbonyl electrophiles. Notably, the diastereoselectivity of this process is enhanced by the presence of water, and DFT calculations support a stereochemical model involving a facially selective protonation of a water-coordinated enol intermediate.
Metal-free SN2a′ decarboxylative rearrangement of β-keto esters
Bizet, Vincent,Lefebvre, Valerie,Baudoux, Jerome,Lasne, Marie-Claire,Boulange, Agathe,Leleu, Stephane,Franck, Xavier,Rouden, Jacques
experimental part, p. 4170 - 4175 (2011/10/02)
Treatment of 2-methoxycarbonyl-(or 3-cyano-)allyl acetoacetates with a tertiary amine or triphenylphosphane afforded α-methylene γ-substituted δ-keto esters (or nitrile) in satisfactory yields. Various bases and nucleophiles were tested to elucidate the m
