51608-62-9

Upstream product

• 10387-93-6 N-(methoxy(phenyl)methyl)benzamide 
• 17599-61-0 N-benzylidene-1,1,1-trimethylsilanamine 
• 98-88-4 benzoyl chloride 
• 120419-97-8 (E)-N-benzylidene-1,1,1-trimethylsilanamine 
• 1816-89-3 2-azido-1-(1,2-diphenyl)ethanone 
• 100-52-7 benzaldehyde 
• 55-21-0 benzamide 
• 117067-48-8 1-benzotriazolyl-N-benzoyl-1-phenylmethylamine 

Downstream Products

• 1485-72-9 N-benzoyl-diphenylmethylamine 
• 263239-91-4 (R)-3-((4R,6S)-2,4-Diphenyl-5,6-dihydro-4H-[1,3]oxazin-6-yloxy)-4,4-dimethyl-dihydro-furan-2-one 
• 263239-93-6 (R)-3-((4R,6R)-2,4-Diphenyl-5,6-dihydro-4H-[1,3]oxazin-6-yloxy)-4,4-dimethyl-dihydro-furan-2-one 
• 263239-95-8 (R)-N-(3-oxo-1-phenylpropyl)benzamide 
• 622851-08-5 (4S,5S)-1,4-diphenyl-5-(3-furyl)-4,5-dihydro-oxazole 
• 861256-13-5 tert-butyl 3-(benzamido)-2-diazo-3-phenylpropanoate 
• 91875-49-9 (S)-N-(3-oxo-1,3-diphenylpropyl)benzamide 
• 91875-49-9 (R)-N-(3-oxo-1,3-diphenylpropyl)benzamide 

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

Asymmetric synthesis of propargylamides via 3,3′-disubstituted binaphthol-modified alkynylboronates

(Chemical Equation Presented) Alkynylboronates derived from 3,3′-disubstituted-2,2′-binaphthols react with various N-acylimines to give the expected chiral propargylamides with up to 99% ee. This new methodology was applied to the first enantioselective s

Solid-state photolysis of α-azidoacetophenones

(Chemical Equation Presented) Solid-state photolysis of 1 yields 2 in a crystal-to-crystal reaction. The reaction takes place by α-cleavage to form a benzoyl and an azido alkyl radical pair. The azido alkyl radicals rearrange into iminyl radicals and N2. The iminyl and benzoyl radicals are held in close proximity within the crystal lattice, which allows them to combine and form 2. X-ray structure analysis, molecular modeling and trapping studies support this mechanism.

N-propargylamides via the asymmetric Michael addition of B-alkynyl-10-TMS-9-borabicyclo[3.3.2]decanes to N-acylimines

The asymmetric synthesis of N-propargylamides through Michael addition of the alkynylborane 1 to N-acylimines is reported. The N-acetylimines provide the best substrates for the process exhibiting high selectivity (56-95% ee) with predictable stereochemis

Organocatalytic asymmetric direct alkylation of α-diazoester via C-H bond cleavage

A new variant of phosphoric acid-catalyzed C-C bond forming reaction, direct alkylation of α-diazoester, via C-H bond cleavage is presented. The resulting products, β-amino-α-diazoesters, are highly functionalized and useful synthetic precursors for vario

Asymmetric Sulfur Ylide Mediated Aziridination: Application in the Synthesis of the Side Chain of Taxol

(Formula presented). Sulfur ylide methodology has been used to construct the Taxol side chain with a high degree of enantioselectivity via a trans-aziridine followed by stereospecific rearrangement of the trans-benzoylaziridine into a trans-oxazoline.

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

First asymmetric synthesis of a 6-alkoxy-5,6-dihydro-1,3-oxazine: A promising enantioselective route to β-amido aldehydes

equation presented The 1,3-oxazine route to enantiopure β-amido aldehydes was investigated. Heterocycloaddition of the N-acyl imine 1 with (R)-O-vinylpantolactone provided the stable dihydroxazine 4c. High diastereocontrols were observed when using Yb(fod)3-catalyzed or SnCl4-mediated conditions, thus leading after quantitative hydrolysis to (R)-N-benzoyl-3-phenylpropanal with >98% ee.