1,3-Dipolar cycloaddition of nitrones with phenylvinyl sulfone. An experimental and theoretical study

Domino Elimination/Nucleophilic Addition in the Synthesis of Chiral Pyrrolidines

“…In the absence of additives, isoxazolidines 7 and 8 are obtained as the major regioisomeric system. However, the proportion of the pair 5 , 6 increases if a coordinating agent (HMPA) is present in the reaction . Although several conditions were tested, no special endo/exo selectivity was observed, and only the ratios of the different isoxazolidines were slightly effected.…”

“…Nitrone 4 is a versatile starting material that has been used for the synthesis of biologically active compounds and structurally complex molecules with a high degree of selectivity . Recently, we reported the 1,3-dipolar cycloaddition of nitrone 4 with phenylvinylsulfone (Scheme ). In our case, four isoxazolidines, 5 – 8 , were obtained in good yield.…”

Crystal structure of (2R*,3aR*)-2-phenylsulfonyl-2,3,3a,4,5,6-hexahydropyrrolo[1,2-b]isoxazole

“…1,3-Dipolar cycloaddition is one of the most useful reaction in organic synthesis (Pellissier, 2007). Nitrones have been used in the synthesis of many kinds of isoxazolidines (Falkowska et al, 2015) by 1,3-dipolar cycloaddition of nitrones with sulfones (Flores, García, Garrido, Nieto et al, 2012) and have demonstrate a range of biological activities including antibiotic, gene expression regulation and cancer cell cytotoxicity (Karyakarte et al, 2012). Our research group is interested in the synthesis of isoxazolidines such as the title compound, for application in organic synthesis (Flores et al, 2011a,b;Flores et al, 2013).…”

Regio- and diastereoselectivity of the 1,3-dipolar cycloaddition of α-aryl nitrone with methacrolein. A theoretical investigation

“…Several experimental works supported by theoretical approaches to investigate the regio-, stereo-and diastereoselectivity of the 13DC of nitrones can be found in the literature. [10][11][12][13] The regioselectivity and endo/exo selectivities of the 13DC reaction of 1-pyrroline-1-oxide to methyl cinnamate and benzylidene acetophenone were rationalized through both experimental and theoretical ndings by Acharjee et al 11 Flores et al 12 undertook a theoretical study of 13DCs of phenylvinylsulfone and several nitrones in order to explain the experimental results, including the regiochemistry, diastereoselectivity, and kinetic control. The reaction mechanism of the 13DC of C,N-diphenylnitrone with unsaturated valerolactone under thermal and LA-mediated conditions has been studied by Śnieżek et al 13 using DFT and MP3 methods.…”