1453206-80-8

Basic information

• Product Name: (3R,4S)-tert-butyl 3-(2-((tert-butoxycarbonyl)amino)ethyl)-2,5-dioxo-1,4-diphenylpyrrolidine-3-carboxylate
• CAS NO: 1453206-80-8
• Molecular Weight: 494.588
• Mol File: 1453206-80-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3R,4S)-tert-butyl 3-(2-((tert-butoxycarbonyl)amino)ethyl)-2,5-dioxo-1,4-diphenylpyrrolidine-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S)-tert-butyl 3-(2-((tert-butoxycarbonyl)amino)ethyl)-2,5-dioxo-1,4-diphenylpyrrolidine-3-carboxylate(1453206-80-8)
• EPA Substance Registry System: (3R,4S)-tert-butyl 3-(2-((tert-butoxycarbonyl)amino)ethyl)-2,5-dioxo-1,4-diphenylpyrrolidine-3-carboxylate(1453206-80-8)

Safety Data

• Hazardous Substances Data: 1453206-80-8(Hazardous Substances Data)

Upstream product

• 459817-82-4 2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester 
• 26690-80-2 2-(N-tert-butoxycarbonylamino)ethanol 
• 5176-27-2 N-tert-butyloxycarbonyl-pyrrole 
• 6017-78-3 (+/-)-1-phenyl-3-phenylpyrrolidine-2,5-dione 

Relevant articles and documents

Catalytic asymmetric alkylation reactions for the construction of protected ethylene-amino and propylene-amino motifs attached to quaternary stereocentres

An efficient catalytic and stereoselective method for the direct construction of protected ethylene-amino and propylene-amino scaffolds attached to quaternary stereocentres is reported. Preliminary investigations revealed a mild base catalysed nucleophilic ring opening of N-sulfonyl aziridines using the commercially available phosphazene base 2-tert-butylimino-2-diethylamino-1,3- dimethyl-perhydro-1,3,2-diazaphosphorine (BEMP) was possible and resulted in highly efficient alkylation reactions with a range of methine carbon acids. This reaction could be rendered highly asymmetric (up to 97 % ee) by employing phase-transfer catalysis to control stereoinduction. Incorporation of alkyl substituents onto the aziridine electrophile, resulted in a highly diastereoselective (up to 30:1 d.r.) variant of this methodology. A further extension using N-protected cyclic sulfamidates as the electrophilic component was successful with a range of pro-nucleophiles (up to 96 % ee and 45:1 d.r.) and allowed a range of nitrogen protecting groups (carbamate, sulfonyl, phosphonyl, benzyl) to be incorporated into the alkylation adducts. Finally, the utility of the products have been demonstrated in the synthesis of useful heterocycles and compounds bearing structural components of natural products. Open sesame: The enantio- and diastereoselective nucleophilic ring opening of protected aziridines and cyclic sulfamidates using asymmetric phase-transfer catalysis (PTC) is reported. The ring-opening alkylation reactions create quaternary chiral centres containing ethylene- and propylene-amino motifs in good yields with good to excellent enantioselectivities (see scheme). These reactions are broad in scope and a wide range of pro-nucleophiles are tolerated. Copyright