183718-81-2

Upstream product

• 98-88-4 benzoyl chloride 
• 132127-28-7 N-trimethylsilyl-(4-methoxybenzaldimine) 
• 10374-25-1 N-benzoyl-1-methoxy-1-(p-methoxyphenyl)-methylamine 
• 104-87-0 4-methyl-benzaldehyde 
• 4461-33-0 benzoyl isocyanate 

Downstream Products

• 56674-30-7 2-(benzamido)-2-(4-methoxyphenyl) acetic acid 
• 1000681-29-7 N-((R)-1-(4-methoxyphenyl)but-3-enyl)benzamide 
• 562100-15-6 (S)-N-[1-(4-methoxyphenyl)-2-formylethyl]benzamide 
• 562099-98-3 (4S,6S)-6-[(2R)-3,3-dimethyl-γ-butyrolacton-2-yl]oxy-4-(4-methoxyphenyl)-2-phenyl-5,6-dihydro-4H-1,3-oxazine 

Relevant academic research and scientific papers

The highly enantioselective addition of indoles to N-acyl imines with use of a chiral phosphoric acid catalyst

Equation Presented The highly enantioselective organocatalytic addition of N-benzyl indoles to N-acyl imines is reported. A total of 15 examples with product yield ranging from 89% to 99% and enantioselectivities from 90% to 97% are presented. A chiral ph

Asymmetric allylboration of acyl imines catalyzed by chiral diols

Chiral BINOL-derived diols catalyze the enantioselective asymmetric allylboration of acyl imines. The reaction requires 15 mol % (S)-3,3′-Ph2-BINOL as the catalyst and allyldiisopropoxyborane as the nucleophile. The reaction products are obtained in good yields (75-94%) and high enantiomeric ratios (95:5-99.5:0.5) for aromatic and aliphatic imines. High diastereoselectivities (diastereomeric ratio > 98:2) and enantioselectivities (enantiomeric ratio > 98:2) are obtained in the reactions of acyl imines with crotyldiisopropoxyboranes. This asymmetric transformation is directly applied to the synthesis of Maraviroc, the selective CCR5 antagonist with potent activity against HIV-1 infection. Mechanistic investigations of the allylboration reaction including IR, NMR, and mass spectrometry studies indicate that acyclic boronates are activated by chiral diols via exchange of one of the boronate alkoxy groups with activation of the acyl imine via hydrogen bonding.

High substrate/catalyst organocatalysis by a chiral Bronsted acid for an enantioselective aza-ene-type reaction

(Chemical Equation Presented) Lowering the load: A very small amount of a binaphthol-derived monophosphoric acid organocatalyst accelerates an azaene-type reaction of N-benzoylimines with enecarbamates to provide β-aminoimines with high enantiomeric purit

Novel use of N-benzoyl-N, O-acetals as N-acylimine equivalents in asymmetric heterocycloaddition: An extended enantioselective pathway to β-benzamido aldehydes

For the first time, easily available N-(α-methoxyalkyl)amides were successfully used as synthetic equivalents of N-acylimines in an asymmetric heterocycloaddition process. The facial-controlled formation of 6-alkoxydihydrooxazines was thus achieved by SnC

N-Acyl imine and enamide intermediates in the palladium-catalyzed amidocarbonylation reaction

N-Acyl imines and enamides have been synthesized and subjected to the reaction conditions for palladium-catalyzed amidocarbonylation of aldehydes. These compounds were competent substrates resulting in the formation of N-acyl amino acids; however, the presence of water was found to be necessary. Direct study of the same amidocarbonylation reaction revealed that enamides could be detected during the course of the reaction. A slight enhancement in the yield of the amidocarbonylation is observed in the presence of radical inhibitors ruling out a meaningful radical pathway. The results are most consistent with a mechanism involving complex equilibration of the starting materials to a number of intermediates which can converge to a haloamidal that subsequently undergoes a palladium insertion.