61341-04-6

Upstream product

• 17360-25-7 N-(p-toluenesulfonyl)-L-valine 
• 72-18-4 L-valine 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 83703-82-6 N-[N-(toluene-4-sulfonyl)-L-valyl]-D-valine methyl ester 
• 145192-66-1 N-[N-(toluene-4-sulfonyl)-L-valyl]-Ξ-phenylalanine methyl ester 
• 90303-10-9 (S)-3-Methyl-N-pyridin-4-yl-2-(toluene-4-sulfonylamino)-butyramide 
• 80613-66-7 6-[(S)-3-Methyl-2-(toluene-4-sulfonylamino)-butyrylamino]-2-oxo-2H-chromene-3-carboxylic acid methyl ester 
• 1252017-92-7 (S)-2-[(S)-3-methyl-2-tosylaminobutanoyl]-3-(1H-indol-3-yl)-6-phenyl-3,4-dihydro-1,2,4-triazin-5(2H)-one 
• 1241390-92-0 (S)-2-isopropyl-1-tosylazetidin-3-one 
• 1262053-80-4 (S)-1-[(S)-3-methyl-2-tosylaminobutanoyl]-6-(2-methyl-1H-indol-3-yl)-3-phenyl-1,6-dihydro-1,2,4-triazin-5(4H)-one 

Relevant 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

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

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

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).

Iron- and cobalt-catalyzed arylation of azetidines, pyrrolidines, and piperidines with grignard reagents

Iron- and cobalt-catalyzed cross-couplings between iodo-azetidines, -pyrrolidines, -piperidines, and Grignard reagents are disclosed. The reaction is efficient, cheap, chemoselective and tolerates a large variety of (hetero)aryl Grignard reagents.

Oxazoline-based organocatalyst for enantioselective strecker reactions: A protocol for the synthesis of levamisole

A chiral oxazoline-based or-ganocatalyst has been found to efficiently catalyze asymmetric Strecker reactions of various aromatic and aliphatic N-benzhydrylimines with trime-thylsilyl cyanide (TMSCN) as a cyanide source at -20°C to give α-aminoni-triles in high yield (96%) with excellent chiral induction (up to 98% ee). DFT calculations have been performed to rationalize the enantioselective formation of the product with the organo-catalyst in these reactions. The organo-catalyst has been characterized by single-crystal X-ray diffraction analysis, as well as by other analytical methods. This protocol has been extended to the synthesis of the pharmaceutically important drug molecule levamisole in high yield and with high enantioselectivity.

1,5-rhodium shift in rearrangement of N -arenesulfonylazetidin-3-ols into benzosultams

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.

Amino acid-derived hydroxamic acids as chiral ligands in the vanadium catalysed epoxidation

New sulfonamide-derived hydroxamic acids 7-11 have been developed as chiral ligands for the V-catalysed asymmetric epoxidation, showing high reactivity at subzero temperatures and moderate to good enantioselectivity. The strong accelerating effect exhibited by the ligands of this type can be attributed to the sulfonamide functionality. A range of cinnamyl type allylic alcohols were epoxidised with up to 74% ee. The Royal Society of Chemistry 2005.

Synthesis and structure of lower rim C-linked N-tosyl peptidocalix[4]arenes

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

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

New easily accessible chiral indole ligands

An efficient and large-scale synthesis of indoles 3 and 4 bearing in 2-position opitically active substituents has been carried out according to the methodology introduced by Fuerstner.Furthermore, starting from indole-2-carbaldeyde, 6, the corresponding chiral indole Schiff bases 7, 8 and 9 have been synthesized.The cobalt complex, prepared from 9 and cobalt(II) acetate, has been shown to catalyze the reduction of acetophenone with NaBH4 in an e. e. of 22percent.