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A three-membered ring approach to carbonyl olefination.

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.

SUBMITTER: Niyomchon S

PROVIDER: S-EPMC5653658 | biostudies-literature | 2017 Oct

REPOSITORIES: biostudies-literature

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A three-membered ring approach to carbonyl olefination.

Niyomchon Supaporn S Oppedisano Alberto A Aillard Paul P Maulide Nuno N

Nature communications 20171023 1

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 ...[more]

PMID: 29061994

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