886466-65-5

Upstream product

• 51127-13-0 2-phenyl-4-methyl-4H-oxazolin-5-one 
• 2937-50-0 Allyl chloroformate 
• 98-88-4 benzoyl chloride 
• 2198-64-3 N-benzoyl-L-alanine 
• 13302-43-7 (S)-2-phenyl-4-methyl-5(4H)-oxazolone 

Downstream Products

• 160281-26-5 N-Benzoyl-(S)-α-(2-propenyl)-α-alanine 
• 96886-55-4 (S)-α-allylalanine 
• 84620-27-9 2-phenyl-4-allyl-4-methyl-Δ²-oxazolin-5-one 
• 886466-24-6 4-methyl-5-oxo-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid allyl ester 

Relevant academic research and scientific papers

Palladium-catalyzed asymmetric decarboxylative allylation of azlactone enol carbonates: Fast access to enantioenriched α-allyl quaternary amino acids

We report a fast protocol for the synthesis of enantioenriched quaternary 4-allyl oxazol-5-ones. The key step is a Pd-catalyzed enantioselective Tsuji allylation of azlactone allyl enol carbonates, which can be easily prepared starting from racemic α-amino acids. The use of (R,R)-DACH-phenyl Trost chiral ligand allowed the attainment of the allylated derivatives in very good yields (83–98 %) and with ee up to 85 %. Scaling up the allylation protocol to gram quantities did not affect the yields end ee values. The produced 4-allyl azlactones can be converted into the corresponding quaternary amino acids or submitted to further synthetic elaborations exploiting the allyl moiety as a handle for the attachment of alkyl and aryl groups. After hydrolysis of the azlactone ring, the zwitterionic amino acids can be attained in enantiopure or nearly optically pure form through only one recrystallization step.

Kinetic resolution displaying zeroth order dependence on substrate consumption: Copper-catalyzed asymmetric alcoholysis of azlactones

Kinetic resolution of 4-alkyl-2-aryl-5-oxo-4,5-dihydrooxazole-4-carboxylic acid esters (azlactones 1) were achieved by copper-DTBM-SEGPHOS catalyzed alcoholysis reaction with good selectivity (12 examples). Variation of ee of unreacted substrates 1 and pr