Intertwining Olefin Thianthrenation with Kornblum/Ganem Oxidations: Ene-type Oxidation to Furnish α,β-Unsaturated Carbonyls |
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Authors: | Péter Angyal András M Kotschy Ádám Dudás Dr Szilárd Varga Dr Tibor Soós |
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Institution: | Institute of Organic Chemistry, Research Centre for Natural Sciences, Magyar tudósok körútja 2, 1117 Budapest, Hungary |
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Abstract: | A widely applicable, practical, and scalable synthetic method for efficient ene-type double oxidation of alkenes is reported via a two-step alkenyl thianthrenium umpolung/Kornblum-Ganem oxidation strategy. This chemo- and stereoselective procedure allows easy access to various α,β-unsaturated carbonyls that may be otherwise difficult or cumbersome to synthesize by conventional methods. For α-olefins, this metal-free transformation can be tuned according to synthetic needs to produce either the elusive (Z)-unsaturated aldehydes or their (E) counterparts. Moreover, this strategy has enabled streamlined synthesis of distinct butadienyl pheromones and kairomones. |
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Keywords: | Alkenes Alkenyl Electrophiles C−H Functionalization Oxidation Thianthrenation |
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