146137-33-9

Upstream product

• 108-86-1 bromobenzene 
• 111292-75-2 (4S)-3-((2E)-2-butenoyl)-4-phenyl-1,3-oxazolidin-2-one 
• 75-16-1 methylmagnesium bromide 
• 141209-95-2 (4S)-4-phenyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one 
• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 
• 100-58-3 phenylmagnesium bromide 
• 20989-17-7 (2S)-2-phenylglycinol 
• 98-80-6 phenylboronic acid 
• 148766-15-8 (4S)-N-crotonyl-4-phenyloxazolidin-2-one 
• 2935-35-5 (S)-2-phenylglycine 
• 4593-90-2 3-phenylbutyric acid 

Downstream Products

• 148706-31-4 (S)-3-((2S,3S)-2-Bromo-3-phenyl-butyryl)-4-phenyl-oxazolidin-2-one 
• 160636-94-2 (S)-3-((2R,3S)-2-Azido-3-phenyl-butyryl)-4-phenyl-oxazolidin-2-one 
• 128677-93-0 (2R)-azido-(3S)-phenylbutanoic acid 
• 59905-30-5 threo-D-(2R,3S)-β-methylphenylalanine 
• 772-14-5 (R)-3-phenylbutyric acid 

Relevant academic research and scientific papers

Palladium-Catalyzed Diastereoselective Synthesis of 3-Arylbutanoic Acid Derivatives

The first palladium-catalyzed diastereoselective conjugate addition of arylboronic acids to chiral imides is reported. The catalytic system employing 4-tert-butyloxazolidin-2-one as the chiral auxiliary in a mixed solvent system of MeOH/H2O (1:3) under an air atmosphere provides the optically active 3-arylbutanoic acid derivatives in excellent yields with high diastereoselectivity.

Diastereoselective copper-catalysed 1,4-addition of Grignard reagents to N-enoyl oxazolidinones

Conjugate additions of organometallic reagents to α,β- unsaturated carboxylic acid derivatives give access to numerous β-substituted chiral building blocks. Chiral oxazolidinones serve as useful surrogates of carboxylic function in the asymmetric conjugate addition of Grignard reagents. N-Enoyl oxazolidinones undergo this 1,4-addition with a catalytic amount of copper salt and using either chiral or achiral phosphine ligands. In particular, chiral ferrocenyl phosphane oxazolines proved useful in achieving high diastereoselectivities. The resulting N-acyl oxazolidinones were obtained in good yields and with high diastereoselectivities (up to single diastereomer).

Diastereoselection in the conjugate additions of organocopper reagents to N-enoyloxazolidinones

A survey of conjugate additions of Yamamoto organocopper reagents to N- enoyl-4-substituted oxazolidinones is reported. Diastereofacial selectivity is reversed for 4-phenyl and 4-benzyloxazolidinones of the same relative configuration. Alkenylcopper reage

Exploration for Large-scale Stereoselective Synthesis of Unusual Amino Acids by using 4-Phenyoxazolidin-2-one as a New Chiral Resolution Reagent

Individual isomers of β-branched α-amino acids have been stereoselectively and asymmetrically synthesized in high yield by a new method which uses 4-phenyloxazolidin-2-one as a novel chiral resolution reagent acting simultaneously as the auxiliary.

Diastereospecific tandem Michael-like addition/electrophilic bromination: A one-pot tandem asymmetric synthesis of precursors of unusual amino acids

A systematic series of key intermediates of unusual β-methyl-amino acids have been synthesized by using a modified Evans auxiliary in an asymmetric Michael-like reaction followed by direct bromination in a one-pot reaction.