163010-72-8

Upstream product

• 116126-04-6 (-)-N-((S)-2-hydroxy-1-phenylethyl)benzamide 
• 81912-50-7 (S)-benzoylamino-phenyl-acetic acid methyl ester 
• 2935-35-5 (S)-2-phenylglycine 
• 6175-45-7 2,2-diethoxyacetophenone 
• 98-88-4 benzoyl chloride 
• 15028-39-4 L-2-phenylglycine methyl ester hydrochloride 
• 20989-17-7 (2S)-2-phenylglycinol 

Downstream Products

• 136693-06-6 N-((1S,2R)-2-hydroxy-1-phenyl-3-butenyl)benzamide 
• 136693-02-2 (-)-N-((1S,2S)-2-hydroxy-1-phenyl-3-butenyl)benzamide 
• 74213-58-4 N-[(1R)-2-hydroxy-1-phenylethyl]benzamide 
• 116126-04-6 (-)-N-((S)-2-hydroxy-1-phenylethyl)benzamide 
• 7352-07-0 N-benzoyl-α-phenylglycine 

Relevant academic research and scientific papers

Direct asymmetric reductive amination of α-keto acetals: A platform for synthesizing diverse α-functionalized amines

We report an efficient and straightforward method to synthesize enantio-enriched N-unprotected α-amino acetals via ruthenium-catalyzed direct asymmetric reductive amination. The α-amino acetal products are versatile and valuable platform molecules that can be converted to the corresponding α-amino acids, amino alcohols, and other derivatives by convenient transformations.

Enantiomerically pure N-Boc- and N-benzoyl-(S)-phenylglycinals

Enantiomerically pure N-Boc- and N-benzoyl-(S)-phenylglycinals were prepared by oxidation of the respective alcohols with Dess-Martin periodinane. The glycinals were phosphonylated with lithium O,O-dimethyl phosphonate at -70°C or (MeO)2POTMS a

Stereoselective intramolecular cyclization of allyl and homoallyl benzamide via π-allylpalladium complex catalyzed by Pd(0)

The transformation of acyclic allylic benzamides 4 and homoallylic benzamides 12 to vinyl oxazolines 3 is achieved in the presence of base by the catalysis and Pd(0) in high yield and with high diastereoselectivity. Especially, in the case of homoallylic benzamides 12, trans-oxazolines 3 are formed exclusively or predominantly over cis-oxazolines 8, irrespective of the composition of their stereoisomers. The reaction is believed to proceed via the same π-allylpalladium complex that arises from either primary or secondary allylic acetates. We applied this method to the syntheses of β- amino-α-hydroxy acids 1 and γ-amino-β-hydroxy acids 2, conveniently protected as oxazoline.

Synthesis of taxol and taxotere side chains by 2-(trimethylsilyl)thiazole based homologation of L-phenylglycine

L-Phenylglycine is homologated by the use of 2-(trimethylsilyl)thiazole into (2R,3S)-N-benzoyl- and N-tert-butoxycarbonyl-3-phenylisoserine, which are isolated as acetonide derivatives in 47 and 35% overall yields and with 84 and 90% ee, respectively.