673452-02-3Relevant academic research and scientific papers
Enantioselective synthesis of β2-amino acids using rhodium-catalyzed hydrogenation
Hoen, Rob,Tiemersma-Wegman, Theodora,Procuranti, Barbara,Lefort, Laurent,De Vries, Johannes G.,Minnaard, Adriaan J.,Feringa, Ben L.
, p. 267 - 275 (2007)
A series of protected β2-dehydroamino acids has been prepared in three steps from commercially available starting materials in good yields. These were used as substrates in rhodium-catalyzed asymmetric hydrogenation applying a mixed ligand syst
Investigating the ritter type reaction of α-Methylene-β-hydroxy esters in acidic medium: Evidence for the intermediacy of an allylic cation
Sa, Marcus M.,Ferreira, Misael,Caramori, Giovanni F.,Zaramello, Laize,Bortoluzzi, Adailton J.,Faggion Jr., Deonildo,Domingos, Josiel B.
supporting information, p. 5180 - 5187 (2013/11/06)
The acid-mediated solvolytic transformation of α-methylene-β- hydroxy esters in acetonitrile was investigated. The reaction was shown to involve nucleophilic attack either at the terminal methylene or at the benzylic carbon. Kinetic and theoretical studies were performed to elucidate the possible pathways involved in the formation of the acetamide products, i.e., through an addition-elimination mechanism, a concerted process (SN2 and S N2′), or involving an allylic cation (SN1 and S N1′). The results of the kinetic analysis, including the isotope effect, Hammett plot, and Eyring plot, are in agreement with a proton transfer equilibrium prior to the formation of a benzylic carbenium ion intermediate, which is consistent with a unimolecular stepwise mechanism. Theoretical examination at the DFT level of theory corroborated these findings, with the lowest activation energy being associated with the S N1′-type mechanism. Acid-mediated solvolysis of α-methylene-β-hydroxy esters in acetonitrile to give isomeric allylic acetamides has been investigated. Two pathways for nucleophilic attack, at the terminal methylene or at the benzylic carbon, were identified; both pathways involve an allylic cation, with the lowest activation energy associated with an SN1′-type mechanism. Copyright
A novel, tandem construction of C-N and C-C bonds: Facile and one-pot transformation of the Baylis-Hillman adducts into 2-benzazepines
Basavaiah, Deevi,Satyanarayana, Tummanapalli
, p. 32 - 33 (2007/10/03)
A novel reaction involving tandem construction of C-N and C-C bonds via the simultaneous Ritter and Houben-Hoesch reactions on Baylis-Hillman adducts leading to a convenient, one-pot synthesis of 2-benzazepine derivatives is described. A facile stereoselective transformation of the Baylis-Hillman adducts into (E)- and (Z)-allyl amides is also presented.
