1713-63-9Relevant articles and documents
Assembling contiguous quaternary carbon atoms: Regio- and stereoselective rearrangements in cobalt-directed radical reactions of 1,4-enynes
Melikyan, Gagik G.,Hughes, Rhoda,Rivas, Bianca,Duncan, Kellyanne,Sahakyan, Nare
, p. 242 - 253 (2015)
Radical coupling reactions of Co2(CO)6-complexed 1,4-enynes occur in a regio- and stereoselective fashion, providing access to 3E,7E-decadiene-1,9-diynes in excellent yields (84-99%). The formation of contiguous quaternary carbon ato
Yamagami et al.
, p. 2967,2974 (1971)
Organocatalytic, Asymmetric Eliminative [4+2] Cycloaddition of Allylidene Malononitriles with Enals: Rapid Entry to Cyclohexadiene-Embedding Linear and Angular Polycycles
Brindani, Nicoletta,Rassu, Gloria,Dell'Amico, Luca,Zambrano, Vincenzo,Pinna, Luigi,Curti, Claudio,Sartori, Andrea,Battistini, Lucia,Casiraghi, Giovanni,Pelosi, Giorgio,Greco, Daniela,Zanardi, Franca
, p. 7386 - 7390 (2015/06/30)
A direct aminocatalytic synthesis has been developed for the chemo-, regio-, diastereo-, and enantioselective construction of densely substituted polycyclic carbaldehydes containing fused cyclohexadiene rings. The chemistry utilizes, for the first time, remotely enolizable π-extended allylidenemalononitriles as electron-rich 1,3-diene precursors in a direct eliminative [4+2] cycloaddition with both aromatic and aliphatic α,β-unsaturated aldehydes. The generality of the process is demonstrated by approaching 6,6-, 5,6-, 7,6-, 6,6,6-, and 6,5,6-fused ring systems, as well as biorelevant steroid-like 6,6,6,6,5- and 6,6,6,5,6-rings. A stepwise reaction mechanism for the key [4+2] addition is proposed as a domino bis-vinylogous Michael/Michael/retro-Michael reaction cascade. The utility of the malononitrile moiety as traceless activating group of the dicyano nucleophilic substrates is demonstrated.
Reduction of nitriles into aldehydes using a TMDS/V(O)(OiPr)3 reducing system
Laval, Stéphane,Dayoub, Wissam,Pehlivan, Leyla,Métay, Estelle,Delbrayelle, Dominique,Mignani, Gérard,Lemaire, Marc
, p. 23 - 26 (2014/01/06)
A simple and convenient method for the chemoselective reduction of nitriles into aldehydes using a 1,1,3,3-tetramethyldisiloxane (TMDS)/ triisopropoxyvanadium(V) oxide reducing system is described. Aromatic as well as aliphatic nitriles are reduced into the corresponding aldehydes in moderate to good yields.