159999-60-7Relevant academic research and scientific papers
Phosphinic Dehydrodipeptides: Diversification of the P1′ Residue with the Morita–Baylis–Hillman Acetates and Inhibition of Alanyl Aminopeptidases
Talma, Micha?
, p. 2109 - 2117 (2020)
Activated allyl acetates (the Morita–Baylis–Hillman acetates) were confirmed as convenient electrophilic precursors of the P1′ fragment of phosphinic dehydrodipeptides, and then, their selected saturated analogs were obtained in the subsequent reduction. This approach is particularly appropriate for structurally complex side chains and thus is an alternative to the addition of α-substituted acrylates with aminoalkylphosphinic acids. While phosphinic dehydrodipeptides were found to be good inhibitors of two mammalian alanyl metalloaminopeptidases, the saturated compounds showed higher activities than their structurally constrained counterparts. Docking calculations and molecular modeling showed that conformational freedom allowed for the favorable binding of distinct stereoisomers of phosphinates, while the presence of the double bond was more restrictive.
Synthesis of chiral β2-amino acids by asymmetric hydrogenation
Luehr, Susan,Holz, Jens,Zayas, Odalys,Wendisch, Volkmar,Boerner, Armin
, p. 1301 - 1319 (2012/11/07)
The synthesis of chiral β2-amino acids by homogeneous asymmetric hydrogenation is discussed. Prochiral β-aryl- or β-hetaryl-α-N-benzyl/N-acetyl/N-Boc substituted α- aminomethylacrylates used as substrates were prepared by a Baylis-Hillman react
Iodine-mediated intramolecular electrophilic aromatic cyclization in allylamines: A general route to synthesis of quinolines, pyrazolo[4,3-b] pyridines, and thieno[3,2-b]pyridines
Batchu, Harikrishna,Bhattacharyya, Soumya,Batra, Sanjay
supporting information, p. 6330 - 6333 (2013/02/23)
An unprecedented synthesis of aromatic ring annulated pyridines from suitably substituted primary allylamines via intramolecular electrophilic aromatic cyclization mediated by molecular iodine under mild conditions is described.
Asymmetric synthesis of 2-alkyl-3-phosphonopropanoic acids via P - C bond formation and hydrogenation
Badkar, Pallavi A.,Rath, Nigam P.,Spilling, Christopher D.
, p. 3619 - 3622 (2008/02/12)
Allylic acetates, formed by the acetylation of Baylis Hillman adducts, undergo addition of phosphorus nucleophiles to give stereoselectively the Z-unsaturated esters. TFA cleavage of the fert-butyl ester and asymmetric hydrogenation of the unsaturated aci
