117470-83-4Relevant articles and documents
Palladium-Catalyzed Highly Chemoselective Intramolecular C-H Aminocarbonylation of Phenethylamines to Six-Membered Benzolactams
Taneda, Hiroshi,Inamoto, Kiyofumi,Kondo, Yoshinori
, p. 2712 - 2715 (2016/06/15)
A palladium-catalyzed highly selective intramolecular C-H aminocarbonylation of Br-functionalized phenethylamines in the presence of CO was achieved while leaving the C-Br bond unreacted to afford six-membered benzolactams with good to high yields. The re
PROCESS FOR PRODUCING AMINO ACID AND DERIVATIVE THEREOF WITH OPTICALLY ACTIVE QUATERNARY AMMONIUM SALT HAVING AXIAL ASYMMETRY
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Page/Page column 98-99, (2008/06/13)
A method of synthesizing an optically active amino acid and a derivative thereof in a two-phase system consisting of a water-immiscible medium and an alkaline aqueous solution using as a phase-transfer catalyst an optically active quaternary ammonium salt
SYNTHESIS OF α-METHYLHISTIDINE BY CATALYTIC PHASE-TRANSFER ALKYLATIONS
O'Donnell, Martin J.,Rusterholz, David B.
, p. 1157 - 1166 (2007/10/02)
α-Methylhistidine was prepared by two complementary routes using a catalytic phase-transfer alkylation procedure.Construction of the product was achieved either by alkylation of an alanine Schiff base ester with an imidazole-containing electrophile or by
Acidities of Glycine Schiff Bases and Alkylation of Their Conjugate Bases
O'Donnell, Martin J.,Bennett, William D.,Bruder, Willian A.,Jacobsen, William N.,Knuth, Keith,et al.
, p. 8520 - 8525 (2007/10/02)
Equilibrium acidities in Me2SO are reported for six ketimines of the type Ph2C=NCH(R)CO2Et and five aldimines, ArCH=NCH(R)CO2Et.Changing R in the ketimine from H to Ph increased the pKa by 2.2 units.This surprising acidity decrease for Ph substitution points to a substantial increase in steric effect, as do the increases in pKa of 3.8 and 4.2 units observed for the replacement of hydrogen by Me and PhCH2, respectively.Phase-transfer alkylation of the Ph2C=NCH2CO2Et ketimine gave over 90 percent of monoalkylate whereas, under similar conditions, the aldimine 4-ClC6H4CH=NCH2CO2Et gave a mixture of mono- and dialkylate.The difference is that the pKa of the monoalkylated aldimine is essentially the same as that of the parent, which leads to rapid equilibration with the parent anion and consequent dialkylation.The rates of alkylation in Me2SO of these parent and monoalkylated anions did not differ greatly, showing that the relative pKHAs of the parent acid and its monoalkyl derivative, rather tham the relative rates of the mono- and dialkylation reactions, is the principal factor that determines the extent of the competition between monoalkylation and dialkylation.
α-METHYL AMINO ACIDS BY CATALYTIC PHASE-TRANSFER ALKYLATIONS
O'Donnell, Martin J.,LeClef, Brigitte,Rusterholz, David B.,Ghosez, Leon,Antoine, Jean-Pierre,Navarro, Mirtha
, p. 4259 - 4262 (2007/10/02)
The α-methyl amino acids, α-methyl p-chlorophenylalanine, α-methyl p-tyrosine, α-methyl m-tyrosine and α-methyl DOPA have been prepared in good yields from amino ester hydrochlorides.The key step in the method is the catalytic phase-transfer alkylation of Schiff base derivatives of monoalkyl amino acids.