Beilstein J. Org. Chem.2018,14, 1028–1033, doi:10.3762/bjoc.14.89
alkene functionalization utilizing a PhI(OAc)2 ((diacetoxyiodo)benzene, PIDA)/Lewis acid combination in order to access isoxazoline and pyrazoline cores. Based on allyl ketone oximes and allyl ketone tosylhydrazones, we have developed an alkene oxyamidation and amido-amidation protocol en route to
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Keywords: amido-amidation; hypervalent iodine; isoxazoline; metal-free; oxyamidation; pyrazoline; Introduction
Isoxazoline and pyrazoline-containing heterocycles are abundant in natural products and biologically active molecules [1][2][3][4][5]. Thus, these scaffolds are also important from the standpoint
)-mediated Ritter-type oxyamidation and amido-amidation of terminal alkenes in the presence of a Lewis acid.
Optimization studies of this Ritter-type oxyamidation commenced with oxidant screening in the presence of a Lewis acid (Table 1). Without oxidant, the Ritter-type oxyamidation still proceeded to give
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Graphical Abstract
Scheme 1:
Hypervalent iodine-mediated heterofunctionalization of terminal alkenes.