223905-86-0

Upstream product

• 100-39-0 benzyl bromide 
• 210972-39-7 N-(p-toluenosulfonyl)-2-hydroxymethylaziridine 
• 127-65-1 chloramine-T 
• 14593-43-2 benzyl allyl ether 
• 702711-42-0 (2R)-1-N-(4-methylphenylsulfonyl)amino-3-(phenylmethoxy)-propan-2-ol 
• 70-55-3 toluene-4-sulfonamide 
• 2930-05-4 (S)-benzyl glycidyl ether 

Downstream Products

• 1019779-22-6 N-(1-benzyloxymethyl-4-[1,3]dioxolan-2-yl-butyl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Modular One-Step Three-Component Synthesis of Tetrahydroisoquinolines Using a Catellani Strategy

Reported is a modular one-step three-component synthesis of tetrahydroisoquinolines using a Catellani strategy. This process exploits aziridines as the alkylating reagents, through palladium/norbornene cooperative catalysis, to enable a Catellani/Heck/aza-Michael addition cascade. This mild, chemoselective, and scalable protocol has broad substrate scope (43 examples, up to 90 % yield). The most striking feature of this protocol is the excellent regioselectivity and diastereoselectivity observed for 2-alkyl- and 2-aryl-substituted aziridines to access 1,3-cis-substituted and 1,4-cis-substituted tetrahydroisoquinolines, respectively. Moreover, this is a versatile process with high step and atom economy.

Synthesis of hexahydro-1H-benzo[c]chromen-1-amines via the intramolecular ring-opening reactions of aziridines by π-nucleophiles

The intramolecular cyclization of aziridines with π-nucleophiles can be a useful route to a number of heterocyclic and carbocyclic systems. This methodology has been applied to the synthesis of hexahydro-1H-benzo[c]chromen-1- amines, the basic skeleton of many amaryllidaceae alkaloids. The success of the aziridine cyclization is largely dependent on the N-substitution of aziridine, with activated aziridines not undergoing the cyclization reaction. Only N-H-, N-alkyl- and N-arylaziridines underwent the cyclization reaction. The ring opening of an unactivated aziridines with a π-nucleophile is one of the first examples of such a reaction. Georg Thieme Verlag Stuttgart.

Synthesis of N-sulfonyl aziridines through regioselective opening of epoxides under solid-liquid PTC conditions

The ring opening of epoxides 1 with 4-toluenesulfonamide (6) under solid-liquid phase transfer catalysis (SL-PTC) conditions afforded regioselectively β-sulfonamidoalcohols 7 in high yields. These were further convened into N-sulfonylaziridines 9 after ac