A three-membered ring approach to carbonyl olefination

Supaporn Niyomchon, Alberto Oppedisano, Paul Aillard and Nuno Maulide ()
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Supaporn Niyomchon: University of Vienna
Alberto Oppedisano: University of Vienna
Paul Aillard: University of Vienna
Nuno Maulide: University of Vienna

Nature Communications, 2017, vol. 8, issue 1, 1-7

Abstract: Abstract The carbon–carbon double bond, with its diverse and multifaceted reactivity, occupies a prominent position in organic synthesis. Although a variety of simple alkenes are readily available, the mild and chemoselective introduction of a unit of unsaturation into a functionalized organic molecule remains an ongoing area of research, and the olefination of carbonyl compounds is a cornerstone of such approaches. Here we show the direct olefination of hydrazones via the intermediacy of three-membered ring species generated by addition of sulfoxonium ylides, departing from the general dogma of alkenes synthesis from carbonyls. Moreover, the mild reaction conditions and operational simplicity of the transformation render the methodology appealing from a practical point of view.

Date: 2017
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DOI: 10.1038/s41467-017-01036-y

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