149286-01-1

Upstream product

• 96-09-3 styrene oxide 
• 70-55-3 toluene-4-sulfonamide 
• 100-42-5 styrene 
• 144-86-5 N-chloro-4-methylbenzenesulfonamide 
• 30057-92-2 N-(p-toluenesulfonyl)aminoacetophenone 
• 24395-14-0 N-(p-tolylsulfonyl)-2-phenylaziridine 
• 34889-55-9 3-[(4-methylphenyl)sulfonyl]-5-phenyl-1,3-oxazolidin-2-one 
• 124-38-9 carbon dioxide 
• 127-65-1 chloroamine-T 
• 20989-17-7 Phenylglycinol 
• 98-59-9 p-toluenesulfonyl chloride 
• 100-52-7 benzaldehyde 
• 68-12-2 N,N-dimethyl-formamide 
• 133522-24-4 (R)-4-Phenyl-[1,3,2]dioxathiolane 2-oxide 

Downstream Products

• 2549-14-6 (R)-2-Amino-1-phenylethanol 
• 1092363-46-6 C₂₀H₂₅NO₄S 
• 697287-96-0 4-methyl-N-(2-oxo-2-phenylethyl)-N-(prop-2-yn-1-yl)benzenesulfonamide 

Relevant academic research and scientific papers

Efficient ring opening reactions of N-tosyl aziridines with amines and water in presence of catalytic amount of cerium(IV) ammonium nitrate

While methyl- and benzylamines opened N-tosyl aziridines 1 very efficiently in acetonitrile with complete regio- and stereoselectivity to give the corresponding diamines 2 and 3, respectively, in excellent yields, similar openings with water could only be achieved in the presence of a catalytic amount of cerium(IV) ammonium nitrate under very mild conditions furnishing the amino alcohols 4.

Synthesis of 2-Aminophosphates via SN2-Type Ring Openings of Aziridines with Organophosphoric Acids

The synthesis of 2-aminophosphates is achieved by a SN2-type ring opening reaction of various N-protected or free aziridines with phosphoric acids in a regiospecific and/or enantiospecific way. A one-pot, two-step procedure is also developed enabling direct access to 2-aminophosphates from olefins without isolation of the aziridine intermediates.

Conversion of aziridines to oxazolidines through geminal difunctionalization of vinyl arenes or by tandem ring-opening/closing reaction of aziridine itself

One pot synthesis of 1,3-oxazolidines derivatives was developed by two different approaches. Aziridines were used in the first approach instead of amino alcohol. Whereas, in the second approach we have developed an unprecedented reaction where aziridine i

Ceric ammonium nitrate (CAN) catalyzed ring cleavage of N-tosyl aziridines: A potential tool for solution phase library generation

A range of N-tosylaziridines is cleaved with NaN3, H2O, MeOH to synthesize vicinal azidoamines, aminols and amino ethers in good to excellent yields catalyzed by ceric ammonium nitrate and used in solution phase library synthesis.

Zirconyl nitrate mediated regioselective ring opening of epoxides and aziridines: an easy synthesis of β-nitrato-alcohols and -sulfonamides

Epoxides and aziridines are cleaved efficiently and regioselectively in the presence of zirconyl nitrate at room temperature to afford the corresponding β-nitrato-alcohols and -sulfonamides, respectively, in high yields.

A tandem process for the synthesis of β-aminoboronic acids from aziridines with haloamine intermediates

An unprecedented synthetic strategy is devised to generate β-aminoboronic acids from aziridines via a sequential process involving 1,2-iodoamine formation and radical borylation under light irradiation. A variety of aziridines including multiply substituted aziridines have been successfully employed as synthetic precursors, expanding their synthetic utility compared to previous methods. Mechanistic studies suggest that the boron source plays a unique role in the borylation step, and in the formation of haloamine intermediates.

Cobalt-Catalyzed Hydroalkynylation of Vinylaziridines

Transition metal-catalyzed hydroalkynylation reactions are efficient transformations allowing the straightforward formation of functionalized alkynes. Therein, we disclose the cobalt-catalyzed hydroalkynylation of vinylaziridines giving rise to both linea

Visible-light-triggered Catalytic Halohydrin Synthesis from Epoxides and Trichloroacetonitrile by Copper and Iron Salts

Preparation of vicinal halohydrins, in which copper or iron chlorides catalyze the ring-opening reaction of epoxides with visible light effectively, is described. The use of trichloroacetonitrile as a halogen source enables catalytic HCl generation under the mild conditions. This method can also be applied to the aziridine ring-opening reaction.

Double Functionalization of Styrenes by Cu-Mediated Assisted Tandem Catalysis

The double functionalization of styrenes through Cu-mediated assisted tandem catalysis was developed. The reaction was initiated by Cu-catalyzed aziridination and the subsequent nucleophilic ring-opening, which was triggered by the addition of (NH4)2S2O8 as an oxidant of Cu-catalyst to form a variety of C–C and C–X bonds. The expansion to three contiguous catalytic cycles led to the synthesis of functionalized indolines by one-pot operation.

Chiral-Organotin-Catalyzed Kinetic Resolution of Vicinal Amino Alcohols

A highly efficient kinetic resolution of racemic amino alcohols has been achieved for the first time with a chiral tin catalyst. A chiral organotin compound with 3,4,5-trifluorophenyl groups at the 3,3′-positions of the binaphthyl framework enabled this transformation with excellent yield and high enantioselectivity. The process tolerates aryl- and alkyl-substituted amino alcohols and a variety of other substrates, affording the corresponding products in high enantioselectivity and with s factors up to >500.