72002-77-8

Upstream product

• 93-58-3 benzoic acid methyl ester 
• 28143-91-1 (1S,2S)-2-amino-1-phenyl-1,3-diol 
• 93-97-0 benzoic acid anhydride 
• 526214-15-3 4-benzoyl-2-phenyl-4H-oxazol-5-one 
• 41542-84-1 N-(1-hydroxymethyl-2-oxo-2-phenyl-ethyl)-benzamide 
• 115964-09-5 (1RS:2RS)-2-benzamino-3-benzoyloxy-1-phenyl-propanol-⁽¹⁾ 
• 102012-91-9 (1RS,2RS)-1,3-diacetoxy-2-benzoylamino-1-phenyl-propane 
• 3306-06-7 (+/-)-threo-2-amino-1-phenyl-1,3-propanediol 
• 98-88-4 benzoyl chloride 
• 64951-84-4 ethyl trans-4,5-dihydro-2,5-diphenyl-4-oxazolecarboxylate 
• 4190-14-1 N-(2-oxo-2-phenylethyl)benzamide 
• 42267-16-3 threo-DL-β-phenylserine ethyl ester hydrochloride 
• 16735-23-2 3-hydroxy-1-oxo-1-phenylpropan-2-aminium chloride 
• 115964-09-5 (1RS:2SR)-2-benzamino-3-benzoyloxy-1-phenyl-propanol-⁽¹⁾ 

Downstream Products

• 440643-35-6 [(S,S)-2-phenyl-4,5-dihydro-oxazol-4-yl]-phenyl-methanol 
• 548773-02-0 4-Nitro-benzoic acid (R)-phenyl-((S)-2-phenyl-4,5-dihydro-oxazol-4-yl)-methyl ester 
• 3306-06-7 (+/-)-threo-2-amino-1-phenyl-1,3-propanediol 
• 102012-91-9 (1RS,2RS)-1,3-diacetoxy-2-benzoylamino-1-phenyl-propane 
• 101734-34-3 (RS)-4-((RS)-α-acetoxy-benzyl)-2-phenyl-4,5-dihydro-oxazole 
• 3313-16-4 (1RS,2RS)-2-benzoylamino-1,3-bis-benzoyloxy-1-phenyl-propane 
• 102012-91-9 (1S,2S)-1,3-diacetoxy-2-benzoylamino-1-phenyl-propane 

Relevant academic research and scientific papers

Evaluation of chiral oxazolines for the highly enantioselective diethylzinc addition to N-(diphenylphosphinoyl) imines

On the basis of the principle that the incorporation of the structurally rigid and conformationally restricted skeleton in β-amino alcohols is beneficial to the enantioselective diethylzinc addition to imines, a series of chiral oxazolines, which had been

The first use of chiral oxazoline ligands in the highly enantioselective diethylzinc addition to diphenylphosphinoyl imines

A series of chiral oxazolines, which had been conveniently prepared from commercially available (1S,2S)-2-amino-1-phenylpropane-1,3-diol, was applied in the diethylzinc addition to diphenylphosphinoyl imines to give high yields of 68-84% and excellent e.e

1,2-Asymmetric induction in conjugate addition of nitroalkenes

Conjugate addition of nucleophiles to the nitroalkenes 8 and 11 followed by in situ ozonolysis resulted in the formation of α-substituted thioesters exhibiting the 'unexpected' syn relative configuration between the C-3 and newly formed stereogenic centre

Application of the Mitsunobu reaction to ephedrines and some related amino alcohols. Aspects of intramolecular participation of the amino group

Inversion of configuration at the benzylic hydroxyl group of (1S,2S)-pseudoephedrine (2) to afford (1R,2S)-ephedrine is known to be a difficult process.The Mitsunobu reactions of 1 and 2 might offer a route to achieve such inversions.In fact Mitsunobu reactions on 1 and 2 are known to proceed via aziridines formed on intramolecular SN2 substitution by the amine functionality.The Mitsunobu reactions of N-methylated and N-benzylated ephedrines have been found to proceed via the corresponding aziridinium ions.These aziridinium ions can be opened (SN2 substitution) by nucleophiles like phthalimide and thiols.Intramolecular participation in 2 can be avoided by use of the tert-butyloxycarbonyl-(BOC) or benzyloxycarbonyl- (CBZ) protected derivatives.Mitsunobu reactions on these derivatives lead to inversion of configuration at the benzylic hydroxyl center.In contrast the BOC and CBZ derivatives of 1 are deprotected under Mitsunobu conditions.The Mitsunobu reactions of threo (1S,2S)-2-amino-1,3-propanediol have also been examined.An attempt to achieve protection by reaction with dimethylformamide dimethyl acetal led to the more substituted 2-oxazoline as established by X-ray crystallography.The desired inversion of configuration of the benzylic hydroxylic group was eventually achieved by protection of the amino substituent as the phthalimide and protection of the primary hydroxyl group as the tosylate.