66607-69-0

Upstream product

• 555-16-8 4-nitrobenzaldehdye 
• 91-00-9 Benzhydrylamine 

Downstream Products

• 83326-67-4 (2S,3S)-2-Benzhydryl-3-(4-nitro-phenyl)-oxaziridine 
• 83326-67-4 (2S,3R)-2-Benzhydryl-3-(4-nitro-phenyl)-oxaziridine 
• 108860-25-9 4-(p-methoxybenzoyloxy)-4-(p-methoxyphenyl)-3-(p-nitrophenyl)-1,1-diphenyl-2-azabuta-1,3-diene 
• 382142-90-7 cis-1-benzhydryl-(3S)-(4-nitrophenyl)-aziridine-(2S)-carboxylic acid ethyl ester 
• 1176305-52-4 C₂₁H₁₇N₃O₂ 

Relevant academic research and scientific papers

Regulation of orthogonal functions in a dual catalyst system. Subservient role of a nonchiral lewis acid in an asymmetric catalytic heteroatom Diels-Alder reaction

A catalytic asymmetric heteroatom Diels-Alder reaction of unactivated imines with Danishefsky's diene is described which gives high asymmetric induction for N-benzhydryl imines derived from a variety of aldehydes. The catalyst is derived from B(OPh)3 and the VAPOL ligand and gives good induction, but the reaction stalls and does not give high conversion (～50%). It was found that in the presence of both the chiral catalyst and excess amounts of B(OPh)3 the reaction proceeds to completion and gives high yields of the dihydropiperidinone product. Despite the presence of large quantities of the nonchiral Lewis acid B(OPh)3, the asymmetric induction of the product remains constant (90% ee) as the amount of B(OPh)3 is steadily increased and does not drop off until the ratio of B(OPh)3 to VAPOL is 100:1 (82% ee). These observations are interpreted as involving highly separated and different activities for the chiral and nonchiral Lewis acids present in the reaction. Specifically, the excess B(OPh)3 serves to bind to the product and release the chiral catalyst to turnover more starting material. The B(OPh)3 does not compete in turning over the starting material, and a series of binding studies reveal that this is likely due to a combination of two factors. The binding studies reveal that the chiral catalyst binds to the starting imine 7 times more strongly than does B(OPh)3. However, in order to explain the constant asymmetric induction observed despite the addition of increasing amounts of B(OPh)3, the rate of the reaction of the imine complexed with the chiral catalyst must be at least 10 times faster than the reaction of the imine complexed with B(OPh)3. Finally, a catalyst generated from BINOL and B(OPh)3 does not show this phenomenon. Copyright

Indium triflate catalyzed reaction of diisopropyl diazomethylphosphonate with imines as a new approach to cis- and trans-aziridine-2-phosphonates

A new and efficient synthesis of cis- and trans-aziridine-2-phosphonates by metal-catalyzed aziridination reaction of diisopropyl diazomethylphosphonate and substituted aryl imines is reported. By exploring the influence of different Lewis acids employed as catalysts, imine nitrogen substituents, and the solvent effects we conclude that the best results are obtained when N-diphenylmethyl-substituted benzylimines are reacted with diisopropyl diazomethylphosphonate in methylene chloride at 0 °C in the presence of In(OTf)3 as catalyst.

Synthesis of 1,2-dihydropyridines using vinyloxiranes as masked dienolates in imino-aldol reactions

The application of vinyloxiranes, substituted with an electron-withdrawing group, as masked dienolates in vinylogous imino-aldol reactions was achieved. Under the reaction conditions highly substituted 1,2-dihydropyridines were obtained in moderate to good yields. Mechanistic studies indicate that the reaction proceeds via the formation of an (E)-amino-α,β-unsaturated aldehyde, followed by isomerization to the (Z)-isomer, cyclization, and elimination of a water molecule, leading to the formation of the 1,2-dihydropyridine.

An efficient synthesis of (-)-chloramphenicol via asymmetric catalytic aziridination: a comparison of catalysts prepared from triphenylborate and various linear and vaulted biaryls.

[reaction--see text] The antibiotic (-)-choramphenicol has been synthesized in only four steps from p-nitro-benzaldehyde in optically pure form from an asymmetric catalytic aziridination reaction with a chiral catalyst prepared from triphenylborate and the (R)-VAPOL ligand. Catalysts generated from the VAPOL and VANOL ligands give much higher asymmetric induction than do catalysts prepared from 6,6'-diphenylVAPOL, BINOL, and BANOL ligands.

The synthesis of 1-aminobenzylphosphonic acids from benzylidenediphenylmethylamines, for use as structural units in antithrombotic tripeptides

Acid hydrolyses of O,O-dimethyl or O,O-diethyl 1-(diphenylmethylamino) benzylphosphonate intermediates 2, formed from the addition at elevated temperature of dimethyl or diethyl phosphite to benzylidenediphenylmethylamines 1, generates 1-aminobenzylphosphonic acids 3 in good yield.

Aroylation of Carbanions Derived from N-(Diphenylmethyl)arylmethanimines. A Synthesis of 4-Aroyloxy-2-azabuta-1,3-dienes

The acylation of carbanions derived from N-(diphenylmethyl)arylmethanimines using aroyl chlorides, allows the preparation of a new type of substituted 2-azabuta-1,3-dienes in which the imino group is conjugated with an enol ester.The reaction is quite general and facilitates the preparation of a wide range of 2-azadienes with electron-donating and electron-withdrawing groups on the phenyl rings.The site selectivity for the attack of the electrophile on the aza-allyl anion can be controlled by the substituents on the carbanion and on the hardness of the electrophile.

Spectral Studies of Benzaldehyde N-Benzhydrylimines

Effect of substituents in the benzylidene part of some benzaldehyde N-benzhydrylimines on the IR, UV and PMR spectra has been discussed and a rationale for the observed data presented.