Facile Conversion of Cyclopropanols into Linear Conjugate Enones

Han, Wenjuan; Li, Shaogang; Lu, Xinmin

doi:10.1002/ejoc.201402175

Cited by 18 publications

(8 citation statements)

References 54 publications

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“…The preparation of conjugated enones from cyclopropyl alcohols has been also been explored by Wu and co-workers. 174 This stepwise procedure first involves the cobalt-catalyzed ring opening of the cyclopropyl alcohol 325 to form the β-keto radical, followed by trapping with molecular oxygen to form the hydroperoxide product 326. Upon addition of PPh 3 , this product was reduced to the β-hydroxy ketone 327 and then directly treated with MsCl and Et 3 N to yield the desired conjugated enone 328 (Scheme 78).…”

Section: C−c Bond Cleavage To Generate β-Ketomentioning

confidence: 99%

“…The preparation of conjugated enones from cyclopropyl alcohols has been also been explored by Wu and co-workers . This stepwise procedure first involves the cobalt-catalyzed ring opening of the cyclopropyl alcohol 325 to form the β-keto radical, followed by trapping with molecular oxygen to form the hydroperoxide product 326 .…”

Section: C–c Bond Cleavage To Generate β-Keto Radicalsmentioning

confidence: 99%

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Selective Carbon–Carbon Bond Cleavage of Cyclopropanols

et al. 2020

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The carbon–carbon (C–C) bond cleavage of cyclopropanols is a wide area of research with much current activity. This review highlights new developments in this area over the past two decades. A summary is made of the three main reactivity modes, namely, homoenolate chemistry, β-keto radical chemistry, and acid-catalyzed ring-opening, as well as all other methods for the C–C bond cleavage and functionalization of cyclopropanols, including base-mediated ring-opening, metal-catalyzed C–C insertions and eliminations, oxidative fragmentation using hypervalent iodine reagents, reactions of donor–acceptor cyclopropanols, and pericylic reactions. Emphasis is placed on the synthetic utility of cyclopropanols and related derivatives, which have emerged as unique three-carbon synthons.

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Section: C−c Bond Cleavage To Generate β-Ketomentioning

confidence: 99%

Section: C–c Bond Cleavage To Generate β-Keto Radicalsmentioning

confidence: 99%

Selective Carbon–Carbon Bond Cleavage of Cyclopropanols

et al. 2020

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“…In 2014, a practical method for the conversion of 1,2-disubstituted cyclopropanols 91 derived from Kulinkovich cyclopropanation into linear enones 147 was developed by Wu and co-workers [121]. The approach features the regioselective cleavage of the cyclopropane rings in EtOH at room temperature with cheap and readily available Co(acac) 2 as the catalyst and air as the reagent (Scheme 41).…”

Section: Reviewmentioning

confidence: 99%

Oxidative radical ring-opening/cyclization of cyclopropane derivatives

Liu

Wang

Chen

et al. 2019

Beilstein J. Org. Chem.

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The ring-opening/cyclization of cyclopropane derivatives has drawn great attention in the past several decades. In this review, recent efforts in the development of oxidative radical ring-opening/cyclization of cyclopropane derivatives, including methylenecyclopropanes, cyclopropyl olefins and cyclopropanols, are described. We hope this review will be of sufficient interest for the scientific community to further advance the application of oxidative radical strategies in the ring-opening/cyclization of cyclopropane derivatives.

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“…Fourteen examples on poly-functionalized structures were reported with yields given between 69 and 92% over a 3 step sequence. 108…”

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confidence: 99%