58107-41-8Relevant academic research and scientific papers
Asymmetric Transfer Hydrogenation: Dynamic Kinetic Resolution of α-Amino Ketones
Gediya, Shweta K.,Clarkson, Guy J.,Wills, Martin
, p. 11309 - 11330 (2020/10/12)
A series of α-amino ketones were reduced using asymmetric transfer hydrogenation (ATH) through a dynamic kinetic resolution (DKR). The protecting group was matched to the reducing agent, and following optimization, a series of substrates were investigated, giving products in high diastereoselectivity, over 99% ee in several cases and full conversion. The methodology was applied to the enantioselective synthesis of an MDM2-p53 inhibitor precursor.
Access to Optically Pure Benzosultams by Superelectrophilic Activation
Michelet, Bastien,Castelli, Ugo,Appert, Emeline,Boucher, Maude,Vitse, Kassandra,Marrot, Jér?me,Guillard, Jér?me,Martin-Mingot, Agnès,Thibaudeau, Sébastien
supporting information, p. 4944 - 4948 (2020/07/14)
Through superacid activation, N-(arenesulfonyl)-aminoalcohols derived from readily available ephedrines or amino acids undergo an intramolecular Friedel-Crafts reaction to afford enantiopure benzosultams bearing two adjacent stereocenters in high yields with fully controlled diastereoselectivity. Low-temperature NMR spectroscopy demonstrated the crucial role played by the conformationally restricted chiral dicationic intermediates.
Chiral-Organotin-Catalyzed Kinetic Resolution of Vicinal Amino Alcohols
Yang, Hui,Zheng, Wen-Hua
supporting information, p. 16177 - 16180 (2019/11/03)
A highly efficient kinetic resolution of racemic amino alcohols has been achieved for the first time with a chiral tin catalyst. A chiral organotin compound with 3,4,5-trifluorophenyl groups at the 3,3′-positions of the binaphthyl framework enabled this transformation with excellent yield and high enantioselectivity. The process tolerates aryl- and alkyl-substituted amino alcohols and a variety of other substrates, affording the corresponding products in high enantioselectivity and with s factors up to >500.
Regiospecific Intermolecular Aminohydroxylation of Olefins by Photoredox Catalysis
Miyazawa, Kazuki,Koike, Takashi,Akita, Munetaka
supporting information, p. 11677 - 11680 (2015/08/11)
A simple and regiospecific aminohydroxylation of olefins by photoredox catalysis has been developed. N-protected 1-aminopyridinium salts are the key compounds and serve as amidyl radical precursors by the action of Ir photocatalysts, fac-[Ir(ppy)3/s
Rhodium complex with unsymmetrical vicinal diamine ligand: excellent catalyst for asymmetric transfer hydrogenation of ketones
Deshpande, Sudhindra H.,Shende, Vaishali S.,Shingote, Savita K.,Chakravarty, Debamitra,Puranik, Vedavati G.,Chaudhari, Raghunath V.,Kelkar, Ashutosh A.
, p. 51722 - 51729 (2015/06/25)
New unsymmetrical vicinal diamine ligands with systematic variation in the regio and stereo positions in the amine and sulphonamide groups were synthesized from cheap starting material such as norephedrine. Catalytic Asymmetric Transfer Hydrogenation (ATH) of aromatic alkyl ketones has been investigated using transition metal complexes and new derivatives of monotosylated unsymmetrical vicinal diamine ligands using sodium formate as the hydrogen source, in water and methanol. Chiral secondary alcohols were obtained with excellent enantioselectivity (>95% ee) and conversion of ketones (>95%) with [Rh(Cp)Cl2]2 and ligand 4 as a catalyst. Enantioselectivity was found to be slightly higher with the use of methanol as a solvent for ATH of ketones with sodium formate as the hydrogen source compared to water as a solvent and was found to be consistent with all the ketones investigated. The reaction mixture is homogeneous in methanol unlike in water, where substrate and product are insoluble in water and form separate phase, sodium formate being soluble in water. The activity and enantioselectivity obtained for ATH of ketones using [Rh(Cp)Cl2]2 and unsymmetrical vicinal diamine ligand as catalyst was comparable with the C2 symmetric benchmark ligands like TsDPEN ((1R,2R)-N-(p-tolylsulfonyl)-1,2-diphenylethylene-diamine), and TsCYDN ((1R,2R)-N-(p-tolylsulfonyl)-1,2-cyclohexyl,diamine) under similar reaction conditions. To the best of our knowledge, this is first example of the ATH of ketones with good activity and high enantioselectivity with [Rh(Cp)Cl2]2 and unsymmetrical vicinal diamine ligands as catalyst systems.
Stereoselective geminal difunctionalization of vinyl arenes mediated by the bromonium ion
Balaji, Pandur Venkatesan,Chandrasekaran, Srinivasan
supporting information, p. 70 - 72 (2014/01/06)
An anti-Markovnikov geminal oxyamination of styrenyl alkenes in an intermolecular fashion using the umpolung strategy mediated by the bromonium ion is reported. Isotope labeling studies confirm the migration of the phenyl group in the semipinacol rearrang
Remarkable enantioselective α-amination in 1-phenyl-2-(N-alkylamino)- 1-propanol
Kumar, Borkatte N. Hitesh,Murugesan, Velayutham,Prakasam, Tangirala,Srinivasan, Pathangi S.,Ramana, Devalla V.
experimental part, p. 262 - 270 (2012/06/01)
(1R,2R)-1-Phenyl-1-alkyl/arylamino-2-(N-alkylamino)propane hydrochloride salts have been synthesized with high degree of enantiomeric purity from (1S,2R)-(+)-1-phenyl-2-(N-alkylamino)-1-propanol through the corresponding chloro derivatives. This reaction sequence involves three inversions with overall inversion of configuration at C-1. Copyright
An annulation reaction for the synthesis of morpholines, thiomorpholines, and piperazines from β-heteroatom amino compounds and vinyl sulfonium salts
Yar, Muhammad,McGarrigle, Eoghan M.,Aggarwal, Varinder K.
, p. 3784 - 3786 (2008/12/23)
(Chemical Equation Presented) Heterocycling: Diphenyl vinyl sulfonium salt 1 acts first as an electrophile, then a base, and then again as an electrophile in this operationally simple, high yielding, one-pot synthesis of pharmacologically important morpholines, thiomorpholines, and piperazines. Compound 1 is an excellent synthon for the 1,2-ethane dication.
Studies on the reaction of aziridines with nitriles and carbonyls: Synthesis of imidazolines and oxazolidines
Gandhi, Shikha,Bisai, Alakesh,Prasad, B. A. Bhanu,Singh, Vinod K.
, p. 2133 - 2142 (2007/10/03)
Reaction of N-tosylaziridines with nitriles and carbonyls to produce imidazolines and oxazolidines has been studied in the presence of a variety of Lewis acids. The reaction is efficient with 1 equiv of BF3· Et2O or Et3OBF4 in CH2Cl 2. However, it is catalytic with metal triflates that give the best results for cycloaddition of N-tosylaziridine with nitriles under solvent free conditions. The same reaction with carbonyls proceeds best in CH 2Cl2 in the presence of molecular sieves. Among various triflates, Zn(OTf)2 has been found to be the best. The cleavage of the N-Ts bond of the cyclized products has been studied in order to make it more versatile in synthesis. The mechanistic aspect of the reaction has been studied by using chiral aziridines as substrates. These formal [3 + 2] cycloaddition reactions of aziridines with nitriles and carbonyls proceed in a Ritter fashion.
A new and direct asymmetric synthesis of a hindered chiral amine via a novel sulfinate ketimine derived from N-tosyl-1,2,3-oxathiazolidme-2-oxide: Practical asymmetric synthesis of (R)-sibutramine
Han, Zhengxu,Krishnamurthy, Dhileepkumar,Senanayake, Chris H.
, p. 327 - 333 (2012/12/22)
A novel and direct approach for the asymmetric synthesis of (R)-sibutramine via chiral amine 5 using N-tosyl-1,2,3-oxathiazolidine-2-oxide (13) as a recyclable chiral auxiliary is described. Chiral sulfinate imine 16e was obtained by treatment of 13e with
