84327-66-2

Upstream product

• 4198-95-2 α-phenylimino-deoxybenzoin 
• 62-53-3 aniline 
• 1439-07-2 trans-Stilbene oxide 
• 5722-91-8 1,2-diphenyl-2-(phenylamino)ethanone 
• 6320-11-2 α-anilino-deoxybenzoin; hydrochloride 
• 1689-71-0 cis-1,2-diphenyloxirane 
• 538-51-2 benzylidene phenylamine 
• 100-52-7 benzaldehyde 

Downstream Products

• 84327-75-3 cis-3,4,5-triphenyl-1,3-oxazolidin-2-one 
• 84344-87-6 2,3,4,7-tetrahydro-5-methoxycarbonyl-2,3,4-triphenyl-1,4-oxazepin-7-one 
• 84327-67-3 (E)-2-[((1R,2S)-2-Hydroxy-1,2-diphenyl-ethyl)-phenyl-amino]-but-2-enedioic acid dimethyl ester 
• 84327-75-3 trans-4,5-diphenyl-3-phenyloxazolin-2-one 
• 84327-67-3 (Z)-2-[((1R,2R)-2-Hydroxy-1,2-diphenyl-ethyl)-phenyl-amino]-but-2-enedioic acid dimethyl ester 
• 84327-67-3 (E)-2-[((1R,2R)-2-Hydroxy-1,2-diphenyl-ethyl)-phenyl-amino]-but-2-enedioic acid dimethyl ester 
• 84327-70-8 (4R,5R)-2-Methoxycarbonylmethyl-3,4,5-triphenyl-oxazolidine-2-carboxylic acid methyl ester 
• 80577-85-1 2-(4-Methoxy-phenyl)-1,5-diphenyl-1H-pyrrole-3,4-dicarboxylic acid dimethyl ester 
• 968-02-5 2,3-trans-1,2,3-triphenylaziridine 
• 84327-70-8 (4R,5S)-2-Methoxycarbonylmethyl-3,4,5-triphenyl-oxazolidine-2-carboxylic acid methyl ester 
• 84327-69-5 2,3,4,7-tetrahydro-5-methoxycarbonyl-2,3,4-triphenyl-1,4-oxazepin-7-one hemiacetal 
• 80577-79-3 4,5-cis-2-(p-methoxyphenyl)-3,4,5-triphenyloxazolidine 
• 99390-04-2 (5R₆S-5S₆R)-4,5,6-triphenylmorpholine-2,3-dione 

Relevant academic research and scientific papers

Thieme chemistry journal awardees-where are they now? bifunctional organocatalysis with N-Formyl-l-proline: A novel approach to epoxide ring opening and sulfide oxidation

A conceptually distinct approach to the aminolysis of 1,2-epoxides, which involves Lewis base-Br?nsted acid catalysis employing N-formyl-l-proline as an easily accessible bifunctional organocatalyst and water as a solvent is presented. The potential of N-formyl-l-proline as organocatalyst for the sulfide oxidation reaction using aqueous hydrogen peroxide as environmentally benign and readily available oxidant is also demonstrated. Good to high yields are achieved for both reactions. Georg Thieme Verlag Stuttgart ? New York.

Enantioselective ring-opening of meso-epoxides by aromatic amines catalyzed by a homochiral metal-organic framework

The enantioselective ring-opening of meso-epoxides by aromatic amines was achieved by using a new chiral metal-organic framework UTSA-32a. The corresponding α-hydroxyamines were obtained with good yields and ee values (up to 89% ee).

Asymmetric ring opening of meso-epoxides with aromatic amines using (R)-(+)-BINOL-Sc(OTf)3-NMM complex as an efficient catalyst

This work reports the asymmetric ring-opening reaction of meso-epoxides with aromatic amines by using the highly efficient in situ generated (R)-(+)-BINOL-Sc(OTf)3-N-methylmorpholine complex. The asymmetric ring opening of cis-stilbene oxide wi

Titanium-mediated cross-coupling reactions of imines with ketones or aldehydes: An efficient route for the synthesis of 1,2-amino alcohols

The cross-coupling reactions of imines with ketones using Ti(O iPr)4/c-C5H9MgCl reagent lead to 1,2-amino alcohols after hydrolysis. The coupling reactions with aldehydes could also afford 1,2-amino alcohols, however, in some cases, aziridines were obtained as major products in a stereoselective manner.

Zinc tetrafluoroborate hydrate as a mild catalyst for epoxide ring opening with amines: Scope and limitations of metal tetrafluoroborates and applications in the synthesis of antihypertensive drugs (RS)/(R)/(S)-metoprolols

The scope and limitations of metal tetrafluoroborates have been studied for epoxide ring-opening reaction with amines, and Zn(BF4) 2?xH2O has been found to be a mild and efficient catalyst affording high yields under solvent-free conditions at rt with excellent chemo-, regio-, and stereoselectivities. The catalytic efficiency followed the order Zn(BF4)2?xH2O ? Cu(BF4)2?xH2O > Co(BF4) 2?6H2O ? Fe(BF4)2? 6H2O > LiBF4 for reactions with cyclohexene oxide and Zn(BF4)2?xH2O ? Co(BF4) 2?6H2O ? Fe(BF4)2? 6H2O > Cu(BF4)2?xH2O for stilbene oxide, but AgBF4 was ineffective. For reaction of styrene oxide with aniline, the metal tetrafluoroborates exhibited comparable regioselectivity (1:99-7:93) with preferential reaction at the benzylic carbon of the epoxide ring. A reversal of regioselectivity (91:1-69:31) in favor of the reaction at the terminal carbon of the epoxide ring was observed for reaction with morpholine. The regioselectivity was dependent on the electronic and steric factors of the epoxide and the pKa of the amine and independent of amine nucleophilicity. The role of the metal tetrafluoroborates is envisaged as "electrophile nucleophile dual activation" through cooperativity of coordination, charge-charge interaction, and hydrogen-bond formation that rationalizes the catalytic efficiency, substrate reactivity, and regioselectivity. The methodology was used for synthesis of cardiovascular drug metoprolol as racemic and enriched enantiomeric forms.

Asymmetric ring opening of meso-epoxides with aromatic amines catalyzed by a new proline-based N,N′-dioxide-indium tris(triflate) complex

The catalytic asymmetric ring opening of meso-epoxides with aromatic amines was achieved using a new proline-based N,N′-dioxide-indium tris(triflate) complex in high yields (up to 99%) with excellent enantioselectivities (up to 99% ee) under mild conditio

Zr(DS)4 as an efficient catalyst for the aminolysis of epoxides in water

Zirconium dodecyl sulfate [Zr(DS)4] is an efficient catalyst for the aminolysis of epoxides in water at pH 5.0. Epoxides and anilines were used and the corresponding β-amino alcohols were isolated in generally high regioselectivity and excellen

Chiral recyclable dimeric and polymeric Cr(III) salen complexes catalyzed aminolytic kinetic resolution of trans-aromatic epoxides under microwave irradiation

Aminolytic kinetic resolution (AKR) of trans-stilbene oxide and trans-β-methyl styrene oxide proceeded smoothly under microwave irradiation using chiral dimeric and polymeric Cr(III) salen complexes as efficient catalysts, giving regio-, diastereo-, and enantioselective anti-β-amino alcohols in high yields (49%) and chiral purity (ee up to 94%) in case of 4-methylaniline within 2 min. The kinetic resolution system is approximately five times faster than traditional oil bath heating at 70°C and 420 times faster than the reaction conducted at room temperature with concomitant recovery of respective chirally enriched epoxides (ee, 92%) in excellent yields (up to 48%). The catalyst 1 worked well in terms of enantioselectivity than the catalyst 2, but both the catalysts were easily recovered and reused five times with the retention of its efficiency.

Catalytic asymmetric ring opening of meso-epoxides with aromatic amines in water

(Chemical Equation Presented) An operationally simple and environmentally benign protocol for the catalytic asymmetric ring opening of meso-epoxides with aromatic amines has been developed. The reactions proceeded smoothly in the presence of 1 mol % of Sc

Zirconium sulfophenyl phosphonate as a heterogeneous catalyst in the preparation of β-amino alcohols from epoxides

A convenient method for the ring opening of epoxides by aromatic amines, catalysed by zirconium sulfophenyl phosphonate in solvent-free conditions, is described.