Dihydrofuran cores are commonly incorporated into synthetically and pharmacologically significant scaffolds in natural product and drug discovery chemistry. Herein, we report a concise and practical strategy to construct spiro-dihydrofuran and amino dihydrofuran scaffolds as anti-vicinal amino alcohol isosteres. Hypervalent iodine (PhI(OAc)(NTs))-mediated C-H activation of alkynes resulted in two-bond formations with one pi bond cleavage: (i) C(sp)-N(sp) and O(sp)-C(sp); (ii) C(sp)-N(sp) and C(sp)-C(sp). The metal-free 5- oxidative cyclization provided versatile amino 2,3- and 2,5-dihydrofurans bearing the C quaternary carbon. The non-toxicity of all synthesised dihydrofurans was verified cell viability assay.
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