75815-80-4

Upstream product

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 67-64-1 acetone 
• 100-42-5 styrene 
• 942-89-2 Acetone O-benzoyloxime 

Downstream Products

• 22184-67-4 1(S)-α-phenylethyldiaziridine 
• 123072-84-4 (R)-4-hydroxy-5-methyl-5-hexen-2-one 
• 142896-45-5 (S)-4-hydroxy-5-methyl-5-hexen-2-one 
• 5381-93-1 (4S)-4-hydroxy-4-phenylbutan-2-one 
• 97799-86-5 1,2,4,6,-tetramethylindole 
• 878887-98-0 (S,R)-N-sec-butyl-α-phenylethylamine 
• 86013-68-5 (S,S)-N-sec-butyl-α-phenylethylamine 
• 31519-47-8 [1-Methyl-prop-(Z)-ylidene]-((S)-1-phenyl-ethyl)-amine 
• 31519-46-7 [1-Methyl-prop-(E)-ylidene]-((S)-1-phenyl-ethyl)-amine 

Relevant academic research and scientific papers

Indoles from 3-Nitropyridinium Salts: A new Route to Chiral Indoles and Indolines

(S)-1-(1-Methylbenzyl)-2,4,6-trimethylindole was prepared by interaction of (S)-isopropyliden(1-methylbenzyl)amine with 1,2,4,6-tetramethyl-3-nitropyridinium iodide.The indoles thus prepared undergo diastereoselective hydride reduction and debenzylation to afford chiral (S)-2,4,6-trimethylindoline with high yield an optical purity up to 76percent.

Synthesis ofN-alkylated lipopeptides and their application as organocatalysts in asymmetric Michael addition in aqueous environments

A library ofN-alkylated lipopeptide organocatalysts were synthesized through an isocyanide-based multicomponent reaction. Various structural motifs were tunably introduced on the catalyst backbone with the aim of incorporating amphiphilic features. Conseq

A Practical Electrophilic Nitrogen Source for the Synthesis of Chiral Primary Amines by Copper-Catalyzed Hydroamination

A mild and practical method for the catalytic installation of the amino group across alkenes and alkynes has long been recognized as a significant challenge in synthetic chemistry. As the direct hydroamination of olefins using ammonia requires harsh conditions, the development of suitable electrophilic aminating reagents for formal hydroamination methods is of importance. Herein, we describe the use of 1,2-benzisoxazole as a practical electrophilic primary amine source. Using this heterocycle as a new amino group delivery agent, a mild and general protocol for the copper-hydride-catalyzed hydroamination of alkenes and alkynes to form primary amines was developed. This method provides access to a broad range of chiral α-branched primary amines and linear primary amines, as demonstrated by the efficient synthesis of the antiretroviral drug maraviroc and the formal synthesis of several other pharmaceutical agents.

Diastereoselective desymmetrization of diarylphosphinous acid-borane amides under Birch reduction

Treatment of diarylphosphinous acid-borane amides possessing chiral amido functionality with an alkali metal solution in liquid ammonia induced a preferential dearomatization of one aryl substituent at phosphorus leading to the formation of non-equimolar amounts of diastereomers. Diastereoselectivity of dearomatization depends strongly on the structure of a chiral auxiliary.

A simple diastereoselective synthesis of chiral nonracemic aliphatic amines

An efficient procedure has been developed for the diastereoselective synthesis of chiral aliphatic amines (diastereoisomeric excess >96%) from (1S)-N-(1-methylethylidene)-1-phenylethylamine, i.e., Schiff base derived from the simplest ketone (acetone) and

Preparation of axially chiral quinolinium salts related to NAD+ models: New investigations of these biomimetic models as 'chiral amide-transferring agents'

The general purpose of this work is to investigate the potential of biomimetic NAD+ models as 'nucleophile-transferring agents' with the ultimate motivation to develop new synthetic tools. This first report focuses on the preparation of an axially chiral quinolinium salt 8. A preliminary investigation of these NAD+ analogues as 'chiral amide-transferring agents' is reported herein. The synthesis of the desired quinolinium salt 8 was first attempted via a Friedlaender approach. Given the poor reproducibility of this first synthetic route, a second strategy making use of an intramolecular nickel-catalyzed coupling was developed with success, furnishing the quinolinium salt 8 in 12% overall yield. The potential of the quinolinium salt 8 as a 'chiral amide-transferring agent' was then investigated. Regioselective 1,4-addition of benzylamine and piperidine produced, respectively, adducts 18a and 18b with high diastereoselectivity (de >95%). The resulting 'chiral masked-amide' 18b was reacted with various activated aryl esters affording the corresponding atropisomeric amide 20 with modest atropenantioselectivity (ee = 2-20%).

Mechanistic insights from ab initio calculations on a nitrogen analogue of the boron-mediated aldol reaction

Molecular orbital calculations were used to study a nitrogen analogue of the boron mediated aldol reaction. Experimental results show that high selectivity can be obtained in some cases, at the cost of low yields. The molecular orbital calculations are us