140706-14-5

Upstream product

• 2026-48-4 (S)-valinol 
• 201230-82-2 carbon monoxide 
• 66107-29-7 4-methoxyphenyl triflate 
• 100-07-2 4-methoxy-benzoyl chloride 
• 916685-58-0 N-(1-hydroxymethyl-2-methyl-propyl)-4-methoxy-benzamide 
• 98-88-4 benzoyl chloride 
• 100-09-4 4-methoxybenzoic acid 

Downstream Products

• 140706-23-6 (-)-(4S)-4,5-dihydro-4-isopropyl-2-(4'-methoxyphenyl)oxazole 

Relevant academic research and scientific papers

Phosphorus-Based Organocatalysis for the Dehydrative Cyclization of N-(2-Hydroxyethyl)amides into 2-Oxazolines

A metal-free, biomimetic catalytic protocol for the cyclization of N-(2-hydroxyethyl)amides to the corresponding 2-oxazolines (4,5-dihydrooxazoles), promoted by the 1,3,5,2,4,6-triazatriphosphorine (TAP)-derived organocatalyst tris(o-phenylenedioxy)cyclotriphosphazene (TAP-1) has been developed. This approach requires less precatalyst compared to the reported relevant systems, with respect to the phosphorus atom (the maximum turnover number (TON) ～30), and exhibits a broader substrate scope and higher functional-group tolerance, providing the functionalized 2-oxazolines with retention of the configuration at the C(4) stereogenic center of the 2-oxazolines. Widely accessible β-amino alcohols can be used in this approach, and the cyclization of N-(2-hydroxyethyl)amides provides the desired 2-oxazolines in up to 99% yield. The mechanism of the reaction was studied by monitoring the reaction using spectral and analytical methods, whereby an 18O-labeling experiment furnished valuable insights. The initial step involves a stoichiometric reaction between the substrate and TAP-1, which leads to the in situ generation of the catalyst, a catechol cyclic phosphate, as well as to a pyrocatechol phosphate and two possible active intermediates. The dehydrative cyclization was also successfully conducted on the gram scale.

Kinetic resolution of vic-amino alcohols catalyzed by a chiral Cu(II) complex

Kinetic resolution of N-benzoylated vic-amino alcohols was achieved by benzoylation in the presence of copper triflate and (R,R)-Ph-BOX as catalysts. The observed enantioselectivity was moderate to high. The method was applied to a kinetic resolution of r

Hammett studies of enantiocontrol by PHOX ligands in Pd-catalyzed allylic substitution reactions

(Matrix presented) Electronically modified PHOX ligands 3a-e were synthesized to probe the mechanism of the enantioselective palladium-catalyzed allylic alkylation and amination reactions. Alkylation with dimethyl sodiomalonate produced only a small variation in the ee (89.3% to 93.4%), but amination with benzylamine gave a much wider variation in the ee (16.4% to 66.6%). Hammett analysis suggests that the substituents interact more significantly with phosphorus and supports a combined electronic and steric basis for enantioselection.

The synthesis of chiral α,β-unsaturated and aryl oxazolines from ketones and arols via their triflates and Pd-catalyzed CO and amino alcohol coupling

An efficient route to the title compounds was achieved using the triflates of ketones and phenols followed by Pd-catalyzed CO insertion in the presence of chiral amino alcohols. Aryl, vinyl bromides and 2-pyridone also served as useful substrates.