34231-55-5Relevant academic research and scientific papers
Hypervalent Iodine(III) Reagent Mediated Regioselective Cycloaddition of Aldoximes with Enaminones
Yoshimura, Akira,Jarvi, Melissa E.,Shea, Michael T.,Makitalo, Cody L.,Rohde, Gregory T.,Yusubov, Mekhman S.,Saito, Akio,Zhdankin, Viktor V.
, p. 6682 - 6689 (2019/11/02)
An efficient oxidative cycloaddition of enaminones with nitrile oxides generated in situ from respective aldoximes using hypervalent iodine reagents has been developed. Reactions of various aldoximes with enaminones in the presence of [hydroxy(tosyloxy)iodo]benzene involved the regioselective cycloaddition reaction resulting in the formation of the 3,4-disubstituted isoxazoles in moderate to good yields. Structures of several isoxazole products were confirmed by a single X-ray crystallography.
Cascade formation of isoxazoles: Facile base-mediated rearrangement of substituted oxetanes
Burkhard, Johannes A.,Tchitchanov, Boris H.,Carreira, Erick M.
, p. 5379 - 5382 (2011/07/08)
Give me five! Nitro compounds and oxetan-3-one react through an intriguing cascade sequence to give isoxazole-4-carbaldehydes using inexpensive reagents in a one-pot procedure (see scheme; Ms=methanesulfonyl). A variety of 3-substituted isoxazole-4-carbaldehydes were obtained in high overall yields.
Cycloadditions of nitrile oxides to α,β-unsaturated aldehydes. Frontier orbital interactions and secondary orbital interactions at work in determining regiochemistry
Toma, Lucio,Quadrelli, Paolo,Perrini, Giancarlo,Gandolfi, Remo,Di Valentin, Cristiana,Corsaro, Antonino,Caramella, Pierluigi
, p. 4299 - 4309 (2007/10/03)
The regiochemistry of the cycloadditions of nitrile oxides to crotonaldehyde and cinnamaldehyde has been determined and is dictated by frontier orbital interactions and secondary orbital interactions as well. In cycloadditions to α,β-unsaturated compounds the directive effect of the frontier orbital interactions can be diverted by steric drifts and secondary orbital interactions. (C) 2000 Elsevier Science Ltd.
