75698-18-9

Upstream product

• 24127-62-6 methyl 2-bromo-3-phenylacrylate 
• 107-11-9 1-amino-2-propene 
• 21788-36-3 (Z)-methyl 2-bromo-3-phenylacrylate 
• 21770-48-9 methyl 2,3-dibromo-3-phenylpropanoate 
• 103-26-4 Methyl cinnamate 

Relevant academic research and scientific papers

A synthesis of aziridines from α-iodoenones

Aziridines were prepared from α-iodocycloenones in very good yield, by a Michael addition/cyclisation (Gabriel-Cromwell) process employing a slight excess of primary amine and Cs2CO3 as base at 95°C. Using chiral amines it was possible to prepare optically pure aziridines. The same method was also efficient for the synthesis of aziridines from acyclic α-halounsaturated compounds. 2-Oxoazabicycles reacted with several nucleophiles to afford α-heteroatom substituted cyclic enones in excellent yield.

Synthesis of N-bridgehead fused bicyclic β-lactams through organometal-mediated transformations of 1,2-dialkenylaziridines

N-Bridgehead fused bicyclic β-lactams have been synthesized through sequential organometal-mediated transformations of 1,2-dialkenylaziridines, namely Co2(CO)8-catalysed carbonylation and ring-closing metathesis (RCM). When firstly subjected to RCM conditions, either with Schrock-Hoveyda or Grubbs' catalyst, 1,2-dialkenylaziridines did not afford the expected bicyclic N-bridgehead products. In contrast, however, cis-1,2-dialkenylaziridines were amenable to carbonylative ring expansion, affording trans-1,4-dialkenyl-β-lactams which could be subsequently metathesized to the corresponding fused bicyclic compounds using Grubbs' catalyst. Unexpectedly, carbonylation of trans-1,2-dialkenylaziridines occurred with the unprecedented rearrangement to the 5,6-dihydro-4H-[1,3]oxazine skeleton.

Synthesis and stereochemistry of 1-alkyl-2-methoxycarbonyl-3-phenylaziridines

Mixtures of cis- and trans-1-alkyl-2-methoxycarbonyl-3-phenylaziridines are formed in the reaction of methyl α-bromocinnmate with excess amine, amino alcohol, and amino acid methyl ester hydrochloride. The ratios of the isomers depend on the solvent used.