142550-25-2

Upstream product

• 540-88-5 acetic acid tert-butyl ester 
• 105590-50-9 t-butyl 3-hydroxy-3-(4-nitrophenyl)propionate 
• 555-16-8 4-nitrobenzaldehdye 
• 1568025-75-1 C₁₁H₁₄N₂O₄ 

Downstream Products

• 1454283-56-7 tert-butyl 3-(4-nitrophenyl)-2H-azirine-2-carboxylate 
• 1454283-78-3 5-tert-butyl 2-ethyl 6-(4-nitrophenyl)-4-phenylpyridine-2,5-dicarboxylate 

Relevant academic research and scientific papers

RhII-catalyzed [3+2] cycloaddition of 2 H-azirines with N-sulfonyl-1,2,3-triazoles

RhII-catalyzed intermolecular [3+2] cycloaddition of 2 H-azirines with N-sulfonyl-1,2,3-triazoles is disclosed, in which a series of fully functionalized pyrroles is produced via rhodium azavinyl carbene intermediates. A distinct feature of this reaction is that the azavinyl carbene serves as a [2 C] equivalent, instead of as [1 C] or aza-[3 C] synthons, which have been reported previously in cyclopropanations and [3 + n] cycloadditions. Moreover, this methodology has also been successfully applied in the total synthesis of URB447 as well as the formal synthesis of Atorvastatin (Lipitor).

Selective α-amination and α-acylation of esters and amides via dual reactivity of O-acylhydroxylamines toward zinc enolates

Selective α-amination and α-acylation of esters and amides have been developed, employing O-acylhydroxylamines as a dually reactive aminating and acylating reagent. Treatment of zinc enolates with O-acylhydroxylamines provides solely 1,3-dicarbonyl compounds under mild conditions. Introduction of a copper catalyst into the system shifts the reactivity entirely, yielding α-amination products exclusively.

Synthesis of pyridines by carbenoid-mediated ring opening of 2H-azirines

Roaming the range: The title reaction tolerates a wide range of substituents on the resulting pyridine ring using mild reaction conditions (see scheme; esp=α,α,α′,α′-tetramethyl-1,3- benzenedipropionic acid). The formation of the key intermediate is catal