56271-34-2Relevant academic research and scientific papers
Iodine-Catalyzed Synthesis of Chiral 4-Imidazolidinones Using α-Amino Acid Derivatives via Dehydrogenative N-H/C(sp3)-H Coupling
Kanyiva, Kyalo Stephen,Tane, Marina,Shibata, Takanori
, p. 12773 - 12783 (2019/09/09)
An efficient method for the asymmetric synthesis of 4-imidazolidinones via an iodine-catalyzed intramolecular N-H/C(sp3)-H activation of readily available and abundant feedstocks, amino acids, and amines is described. The reaction proceeded under visible light irradiation to afford a variety of 4-imidazolidinone derivatives under mild conditions in moderate to excellent yields. Secondary and tertiary C(sp3)-H bonds were aminated, and various functional groups were tolerated.
Metal-Free N–H/C–H Coupling for Efficient Asymmetric Synthesis of Chiral Dihydroquinoxalinones from Readily Available α-Amino Acids
Kanyiva, Kyalo Stephen,Horiuchi, Masashi,Shibata, Takanori
, p. 1067 - 1070 (2018/03/06)
We have developed a method for the synthesis of dihydroquinoxalinones via intramolecular N–H/C–H coupling using hypervalent iodine. The starting materials were prepared from inexpensive and readily available aniline and amino acid derivatives. Various functional groups were tolerated to give multisubstituted dihydroquinoxalinones in moderate to excellent yields. The chirality of the amino acid was transferred to the desired target compound without a loss of enantiomeric excess. Preliminary mechanistic studies indicated that the reaction proceeds via an ionic mechanism.
Palladium-Catalyzed Modular Synthesis of Substituted Piperazines and Related Nitrogen Heterocycles
Montgomery, Thomas D.,Rawal, Viresh H.
, p. 740 - 743 (2016/03/01)
We report here a novel method for the modular synthesis of highly substituted piperazines and related bis-nitrogen heterocycles via a palladium-catalyzed cyclization reaction. The process couples two of the carbons of a propargyl unit with various diamine components to provide nitrogen heterocycles in generally good to excellent yields and high regio- and stereochemical control. (Chemical Equation Presented).
Synthetically amenable amide derivatives of tosylated-amino acids as organocatalysts for enantioselective allylation of aldehydes: Computational rationale for enantioselectivity
Ghosh, Debashis,Sahu, Debashis,Saravanan,Abdi, Sayed H. R.,Ganguly, Bishwajit,Khan, Noor-Ul H.,Kureshy, Rukhsana I.,Bajaj, Hari C.
, p. 3451 - 3460 (2013/06/05)
A phenylalanine derived chiral amide is developed that serves as an effective organocatalyst for the reaction of allyltrichlorosilane with aryl, hetero-aryl and α,β-unsaturated aldehydes to afford the desired homoallylic alcohols in good yield (up to 90%)
1,5-rhodium shift in rearrangement of N -arenesulfonylazetidin-3-ols into benzosultams
Ishida, Naoki,Shimamoto, Yasuhiro,Yano, Takaaki,Murakami, Masahiro
, p. 19103 - 19106 (2014/01/17)
Benzosultams are synthesized in an enantiopure form starting from α-amino acids through a rhodium-catalyzed rearrangement reaction of N-arenesulfonylazetidin-3-ols. Mechanistically, this reaction involves C-C bond cleavage by β-carbon elimination and C-H bond cleavage by a 1,5-rhodium shift.
C2-symmetric recyclable organocatalyst for enantioselective Strecker reaction for the synthesis of α-amino acid and chiral diamine-an intermediate for APN inhibitor
Saravanan,Sadhukhan, Arghya,Khan, Noor-Ul H.,Kureshy, Rukhsana I.,Abdi, Sayed H. R.,Bajaj, Hari C.
experimental part, p. 4375 - 4384 (2012/06/30)
Recyclable chiral amide-based organocatalyst 5 efficiently catalyzed asymmetric Strecker reaction of various aromatic and aliphatic N-benzhydrylimines with ethyl cyanoformate as cyanide source at -10 °C to give a high yield (95%) of α-aminonitriles with excellent chiral induction (ee, up to 99%) with the added advantage of recyclability. Based on experimental observations a probable mechanism was proposed for this reaction. This protocol with catalyst 5 was extended for the synthesis of (R)-phenylalanine and pharmaceutically important drug intermediate (R)-3-phenylpropane-1,2-diamine in high yield with high enantioselectivity.
Reductive aldol and mannich-type reactions of azetidin-3-ones promoted by titanium tetraiodide
Hata, Shingo,Fukuda, Daisuke,Hachiya, Iwao,Shimizu, Makoto
supporting information; experimental part, p. 473 - 477 (2010/08/23)
A convenient method is described for the generation and reaction of the enolates of aminoacetone equivalents, which uses the reduction of azetidin-3-one with titanium tetraiodide and subsequent reactions with electrophiles. This methodology provides a str
Synthesis of some sulphonamide insect juvenile hormone - Part I
Awasthi, Pamita,Mahajan
, p. 1291 - 1297 (2008/12/23)
Regular use of classical insecticides has drastically effected the environment and warm blooded animals. Therefore, there is an urgent need to look for a kind of chemicals which are very specific, targeted in their action and environment friendly. Since l
Synthesis and structure of lower rim C-linked N-tosyl peptidocalix[4]arenes
Sdira, Sofiane Ben,Felix, Caroline P.,Giudicelli, Marie-Beatrice A.,Seigle-Ferrand, Pascal F.,Perrin, Monique,Lamartine, Roger J.
, p. 6632 - 6638 (2007/10/03)
Chiral p-tert-butylcalix[4]arenes functionalized at the lower rim with amino acid residues have been prepared. The 1H and 13C NMR spectra indicate that the macrocycles preferably adopt a cone conformation. Calix[4]arenes bearing amin
Synthesis and structural studies of new N-(p-toluenesulfonyl)amino acid o-phenolamides
Aguilar-Castro, Liliana,Tlahuextl, Margarita,Tapia-Benavides, Antonio R.,Tlahuext, Hugo
, p. 247 - 253 (2007/10/03)
The synthesis and structural studies of N-(p-Toluenesulfonyl)amino acid o-phenolamides was discussed. The structure and conformation of these amides were established by NMR spectroscopy and x-ray crystallography. Variable temperature experiments showed th
