60930-36-1Relevant academic research and scientific papers
Catalytic asymmetric synthesis of diazabicyclo[3.1.0]hexanes by 1,3-dipolar cycloaddition of azomethine ylides with azirines
Adrio, Javier,Carretero, Juan C.,Díaz-Tendero, Sergio,Molina, Alba
supporting information, p. 5050 - 5053 (2020/05/18)
Substituted 1,3-diazabicyclo[3.1.0]hexanes with two contiguous quaternary stereocentres are readily prepared by catalytic asymmetric [3+2] cycloaddition of a-substituted iminoesters with azirines. High diastereoselectivities and enantioselectivities (up to 98% ee) are achieved using CuI/(R)-Fesulphos as the catalytic system.
Enantioselective synthesis of α-secondary and α-tertiary piperazin-2- Ones and piperazines by catalytic asymmetric allylic alkylation
Korch, Katerina M.,Eidamshaus, Christian,Behenna, Douglas C.,Stoltz, Brian M.,Nam, Sangkil,Horne, David
supporting information, p. 179 - 183 (2015/02/05)
The asymmetric palladium-catalyzed decarboxylative allylic alkylation of differentially N-protected piperazin-2- ones allows the synthesis of a variety of highly enantioenriched tertiary piperazine-2-ones. Deprotection and reduction affords the corresponding tertiary piperazines, which can be employed for the synthesis of medicinally important analogues. The introduction of these chiral tertiary piperazines resulted in imatinib analogues which exhibited comparable antiproliferative activity to that of their corresponding imatinib counterparts.
Method for Preparation of Piperazindione Derivatives
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Page/Page column 7, (2011/06/26)
A process for preparing piperazinedione derivatives of the formula I in which R1 is hydrogen, alkyl, alkenyl, alkynyl and alkylcarbonyl,R2 is hydrogen, alkyl, alkenyl, C3-C4-alkynyl and C(═O)R11,Rsup
Influence of ring substitution on the conformation and β-turn mimicry of 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-one peptide mimetics
De Wachter, Rien,Brans, Luc,Ballet, Steven,Van den Eynde, Isabelle,Feytens, Debby,Keresztes, Attila,Toth, Geza,Urbanczyk-Lipkowska, Zofia,Tourwé, Dirk
experimental part, p. 2266 - 2278 (2009/08/08)
Analogs of 4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-ones, containing a methyl substituent at the 4- or 5-position, or a phenyl substituent at C-1, were prepared. Conformational analysis of tetrapeptide models containing these analogs indicated different
Phosphorus-containing aminocarboxylic acids: XIV. Synthesis of analogs of α-substituted glutamic acid
Saratovskikh,Ragulin
, p. 1077 - 1084 (2007/10/03)
Addition of Schiff bases derived from amino acid esters to appropriate vinylphosphoryl compounds, followed by hydrolysis of the adducts formed gives a series of new α-alkylated phosphorus-containing α-aminocarboxylic acids, viz. phosphonic and phosphinic
A Concise Synthesis of Sterically Hindered 3-Amino-2-Oxindoles
O'Connor, Stephen J.,Liu, Zheng
, p. 2135 - 2138 (2007/10/03)
A new method for the synthesis of 3-alkyl-3-amino-2-oxindoles is reported. These compounds are prepared in a 3-step procedure using a base-mediated nucleophilic addition of benzylidene-imine protected α-aminoesters to 2-nitrofluorobenzene as the key step. The process provides a variety of 3-alkyl-3-amino-2-oxindole analogs in yields of 1-24%. Yields are highest with alanine, phenylalanine and 2-pyridylalanine as the amino acid starting materials, while 3-pyridylalanine and O-methyltyrosine are less efficiently arylated. Sterically hindered amino acids such as valine and phenylglycine are for all practical purposes, not substrates for the key nucleophilic substitution reaction. The resulting 3-alkyl-3-amino-2-oxindoles are important intermediates for the preparation of drug-like substances. The conversion of alanine ethyl ester to 3-amino-3-methyl-2-oxindole is described.
