497954-01-5

Basic information

• Product Name: Benzamide, N-[(1S)-1-(hydroxymethyl)-2-phenylethyl]-2-methyl-
• CAS NO: 497954-01-5
• Molecular Formula: C17H19NO2
• Molecular Weight: 269.343
• Mol File: 497954-01-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Benzamide, N-[(1S)-1-(hydroxymethyl)-2-phenylethyl]-2-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, N-[(1S)-1-(hydroxymethyl)-2-phenylethyl]-2-methyl-(497954-01-5)
• EPA Substance Registry System: Benzamide, N-[(1S)-1-(hydroxymethyl)-2-phenylethyl]-2-methyl-(497954-01-5)

Safety Data

• Hazardous Substances Data: 497954-01-5(Hazardous Substances Data)

Upstream product

• 3182-95-4 L-Phenylalaninol 
• 933-88-0 ortho-toluoyl chloride 

Downstream Products

• 776301-22-5 ((S)-4-Benzyl-2,2-dimethyl-oxazolidin-3-yl)-[2-((S)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-ylmethyl)-phenyl]-methanone 
• 776301-21-4 (4S)-2,2-dimethyl-3-o-toluoyl-4-benzyloxazolidine 
• 497954-07-1 (S)-4-benzyl-2-(o-tolyl)-4,5-dihydrooxazole 

Relevant articles and documents

Asymmetric synthesis of 3-substituted 3,4-dihydroisocoumarins via stereoselective addition of laterally lithiated chiral 2-(o-tolyl)oxazolines to aldehydes followed by diastereomer-selective lactonization

Lateral lithiation of (S)-4-isopropyl-2-(o-tolyl)oxazoline in diethyl ether followed by the reaction with aldehydes in the presence of TMEDA produced the addition products with stereoselectivities up to 84% de. Utilization of TMEDA as a ligand is essential for the good selectivity. Rationale for the stereoselectivity is proposed based on ab initio calculation of the lateral lithio species. The major (S,S)-products lactonized faster than the minor (S,R)-products to the corresponding 3,4-dihydroisocoumarins under acidic conditions. Thus, (3S)-3,4-dihydroisocoumarins were obtained in good optical purities up to 97% ee by sequential application of these matched stereoselective reactions.