214280-56-5

Upstream product

• 495-71-6 phenacylacetophenone 
• 70-11-1 α-bromoacetophenone 
• 214280-43-0 Diphenyl-bis-((R)-1-phenyl-allyloxy)-silane 
• 214280-51-0 (4R,7R)-2,2,4,7-Tetraphenyl-4,7-dihydro-[1,3,2]dioxasilepine 
• 104713-12-4 (R)-1-phenylprop-2-en-1-ol 

Downstream Products

• 681144-02-5 (2S,5S)-1-amino-2,5-diphenylpyrrolidine 
• 295328-86-8 (2S,5S)-N-allyl-2,5-diphenylpyrrolidine 
• 1422543-81-4 C₃₉H₄₂N₄ 
• 1422543-84-7 C₃₉H₃₇N₅ 
• 155155-73-0 (R,R)-2,5-diphenylpyrrolidine 
• 1374113-96-8 (2S,5S)-1-[2-(dicyclohexylphosphino)benzylideneamino]-2,5-diphenylpyrrolidine 
• 1374113-95-7 (2S,5S)-1-[2-(dicyclohexylphosphoryl)benzylideneamino]-2,5-diphenylpyrrolidine 
• 1374113-93-5 (2S,5S)-1-[2-(di-o-tolylphosphino)benzylideneamino]-2,5-diphenylpyrrolidine 
• 1374113-92-4 (2S,5S)-1-[2-(di-4-fluorophenylphosphino)benzylideneamino]-2,5-diphenylpyrrolidine 
• 1374113-91-3 (2S,5S)-1-[2-(di-3,5-dimethylphenylphosphino)-benzylideneamino]-2,5-diphenylpyrrolidine 
• 1374113-90-2 (2S,5S)-1-[2-(di-3,5-bistrifluoromethyphenylphosphino)benzylideneamino]-2,5-diphenylpyrrolidine 
• 1374113-89-9 (2S,5S)-1-[2-(di-4-methoxyphenylphosphino)benzylideneamino]-2,5-diphenylpyrrolidine 
• 1374113-77-5 (2S,5S)-1-[2-(diphenylphosphino)benzylideneamino]-2,5-diphenylpyrrolidine 
• 295328-85-7 (2S,5S)‐diphenylpyrrolidine 

Relevant academic research and scientific papers

Asymmetric hydrogenation of 1,4-diketones: facile synthesis of enantiopure 1,4-diarylbutane-1,4-diols

Owing to the biological significance and great synthetic value of 1,4-diarylbutane-1,4-diols and their derivatives, increasingly considerable attention has been paid to developing effective synthetic methods for chiral 1,4-diarylbutane-1,4-diols. We herei

Enantioselective Stetter Reactions Catalyzed by Bis(amino)cyclopropenylidenes: Important Role for Water as an Additive

The first highly enantioselective intermolecular Stetter reaction using simple enones is reported. A series of novel chiral BAC structures were designed and prepared. They were tested in the Stetter reaction with simple aldehydes and enones. The products were generated in excellent yields and enantioselectivities (up to 94% ee). Surprisingly, a substoichiometric amount of water was crucial to obtain high enantioselectivities. Chiral BACs were also shown to catalyze 1,6-conjugate addition reactions with paraquinone methides enantioselectively.

A general, enantioselective synthesis of 2-substituted thiomorpholines and thiomorpholine 1,1-dioxides

In the course of our drug discovery programs, we had need to access chiral, 2-substituted thiomorpholines and their oxidized congeners, thiomorpholine 1,1-dioxides. Here, we disclose a high-yielding, general protocol for the enantioselective synthesis of

Asymmetric Transfer Hydrogenation of (Hetero)arylketones with Tethered Rh(III)-N-(p-Tolylsulfonyl)-1,2-diphenylethylene-1,2-diamine Complexes: Scope and Limitations

A series of new tethered Rh(III)/Cp? complexes containing the N-(p-tolylsulfonyl)-1,2-diphenylethylene-1,2-diamine ligand have been prepared, characterized, and evaluated in the asymmetric transfer hydrogenation (ATH) of a wide range of (hetero)aryl ketones. The reaction was performed under mild conditions with the formic acid/triethylamine (5:2) system as the hydrogen source and provided enantiomerically enriched alcohols with good yields and high to excellent enantioselectivities. Although the nature of the substituents on the phenyl tethering ring did not alter the stereochemical outcome of the reaction, complexes bearing electron-donating groups exhibited a higher catalytic activity than those having electron-withdrawing groups. A scale-up of the ATH of 4-chromanone to the gram scale quantitatively delivered the reduced product with excellent enantioselectivity, demonstrating the potential usefulness of these new complexes.

A general, enantioselective synthesis of N-alkyl terminal aziridines and C2-functionalized azetidines via organocatalysis

A short, high-yielding protocol involving the enantioselective α-chlorination of aldehydes has been developed for the enantioselective synthesis of C2-functionalized aziridines and N-alkyl terminal azetidines from a common intermediate. This methodology allows for the rapid preparation of functionalized aziridines in 50-73% overall yields and 88-94% ee, and azetidines in 22-32% overall yields and 84-92% ee. Moreover, we developed a scalable and cost-effective route to the key organocatalyst (54% overall yield, >95% dr).

Synthesis, characterization and use of a new tethered Rh(III) complex in asymmetric transfer hydrogenation of ketones

A new Rh(III) complex containing the TsDPEN ligand and an η6-arene connected through a carbon tether is reported. The asymmetric transfer hydrogenation of a series of ketones catalyzed by this complex using the formic acid/triethylamine system provided the corresponding alcohols with complete conversions and a high level of enantioselectivity.

Development of chiral bis-hydrazone ligands for the enantioselective cross-coupling reactions of aryldimethylsilanolates

A palladium-catalyzed, enantioselective, aryl-aryl cross-coupling reaction using 1-naphthyldimethylsilanolates and chiral bis-hydrazone ligands has been developed. A family of glyoxal bis-hydrazone ligands containing various 2,5-diarylpyrrolidine groups was prepared to evaluate the influence of ligand structure on the rate and enantioselectivity of the cross-coupling. New synthetic routes to the 1-amino-2,5-diarylpyrrolidines were developed to enable the structure/reactivity-selectivity studies. Role reversal experiments of aryldimethylsilanolates and aryl bromides result in biaryl products with the same configuration and similar enantioselectivities implying that reductive elimination is the stereodetermining step. The origin of stereoselectivity is rationalized through computational modeling of diarylpalldium(II) complex which occurs through a conrotatory motion for the two aryl groups undergoing C-C bond formation.

Mukaiyama-Michael reactions with acrolein and methacrolein: A catalytic enantioselective synthesis of the C17-C28 fragment of pectenotoxins

Enantioselective iminium-catalyzed reactions with acrolein and methacrolein are rare. A catalytic enantioselective Mukaiyama-Michael reaction that readily accepts acrolein or methacrolein as substrates, affording the products in good yields and 91-97% ee, is presented. As an application of the methodology, an enantioselective route to the key C17-C28 segment of the pectenotoxin using the Mukaiyama-Michael reaction as the key step is described.

Design and synthesis of new bis-hydrazones and pyridine bis-hydrazones: Application in the asymmetric Diels-Alder reaction

The design of two different types of new chiral bis-hydrazones 5 (bidentate N,N ligands, type A) and pyridine bis-hydrazones 7 ('pincer' N,N,N ligands, type B) is discussed. Preliminary results on the copper(II)-catalyzed Diels-Alder reaction of N-(E)-crotyloxazolidin-2-one (8) with cyclopentadiene (9) revealed that the (2S,6S)-2,6-diphenylpiperidine C2-symmetric substructure in pyridine bis-hydrazone ligand 7c is the key design element leading to good enantioselectivities. ARKAT-USA, Inc.

Convenient methods for synthesis of C2-symmetric diphenyltetrahydrothiophenes

Racemic and optically pure (-)-(3R,4R)-3,4-diphenyltetrahydrothiophene, (+)-(2S,5S)-2,5-diphenyltetrahydrothiophene, and (-)-(3S,6S)-3,6-diphenyl-1,2- dithiane were synthesized by use, in the crucial steps, of the easy-to-handle borane systems tetrabutylammonium borohydride-iodine and tetrabutylammonium borohydride-iodomethane. Georg Thieme Verlag Stuttgart.