346577-99-9

Upstream product

• 543-27-1 isobutyl chloroformate 
• 183140-29-6 N-isobutyloxycarbonyl-(S)-alanine 
• 3218-36-8 4-Phenylbenzaldehyde 

Downstream Products

• 346578-01-6 (2S,4R)-2-Biphenyl-4-yl-4-(4-bromo-benzyl)-4-methyl-5-oxo-oxazolidine-3-carboxylic acid isobutyl ester 
• 346578-03-8 (R)-3-(4-bromophenyl)-2-isobutoxycarbonylamino-2-methylpropionic acid methyl ester 
• 346578-02-7 (R)-2-isobutoxycarbonylamino-2-methyl-3-phenylpropionic acid methyl ester 
• 346578-00-5 (2S,4R)-4-Benzyl-2-biphenyl-4-yl-4-methyl-5-oxo-oxazolidine-3-carboxylic acid isobutyl ester 

Relevant academic research and scientific papers

Crystallization-induced asymmetric transformations and self-regeneration of stereocenters (SROSC): Enantiospecific synthesis of α-benzylalanine and hydantoin BIRT-377

N-Isobutoxycarbonyl protected L-alanine was condensed with 4-phenylbenzaldehyde in a crystallization-controlled process to give the corresponding cis-oxazolidinone derivative as the sole product in high yield; this underwent enolization and benzylation wi

The formation of a crystalline oxazolidin-5-one from (L)-alanine and its use as a chiral template in the practical synthesis of α-substituted alanine esters

Three different protocols to synthesize oxazolidin-5-ones have been studied with the goal to develop a method to synthesize a diastereomerically pure oxazolidin-5-one. A novel method is reported that uses a dynamic crystallization-induced asymmetric transformation to isolate a single diastereomer of an oxazolidin-5-one in 92% yield on kilogram scale. Alkylation of the oxazolidin-5-one template leads to good-to-excellent yields of N-protected α-substituted alanine esters in >98-99% ee. Schweizerische Chemische Gesellschaft.