ChemInform Abstract: Pd‐Catalyzed Ring Opening of Cyclopropanols.

Okumoto, Hiroshi; Jinnai, Takamitsu; Shimizu, Hidemi; Harada, Yoshinori; Mishima, Hideki; Suzuki, Akira

doi:10.1002/chin.200034084

Cited by 12 publications

(15 citation statements)

References 1 publication

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“…[20][21][22] A report of the same transformation catalyzed by a broad range of palladium catalysts was disclosed independently by Okumoto. 72 The study of the regioselectivity of the process was limited to one example, which nevertheless confirmed the results obtained with 231.…”

Section: Scheme 44 Rhodium-catalyzed [5+2] Cycloaddition Of Iminessupporting

confidence: 74%

Transition-Metal-Catalyzed Rearrangements of Small Cycloalkanes: Regioselectivity Trends in β-Carbon Elimination Reactions

Aïssa¹

2011

Synthesis

162

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In this review, the regioselectivity of transition-metalcatalyzed ring cleavage of cyclopropanes and cyclobutanes by bcarbon elimination is analyzed using experimental results and rationalization models from the literature. Most models proposed are generally consistent with the following trends: Cleavage of the less substituted bond of the small cycloalkane is favored by a minimization of steric hindrance, whereas cleavage of the more substituted bond becomes possible if steric hindrance is limited and if the substituent is electron-withdrawing or if it can coordinate the metal. Importantly, steric congestion can easily offset electronic activation. Moreover, regioselectivity models appear to be more generally applicable to cyclopropanes than to cyclobutanes.

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Section: Scheme 44 Rhodium-catalyzed [5+2] Cycloaddition Of Iminessupporting

confidence: 74%

Transition-Metal-Catalyzed Rearrangements of Small Cycloalkanes: Regioselectivity Trends in β-Carbon Elimination Reactions

Aïssa¹

2011

Synthesis

162

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“…16 Okumoto and co-workers found that this reaction can also be efficiently catalyzed by a number of Pd catalysts, with Pd(dba) 2 (dba = dibenzylideneacetone) giving the desired product 6 in good yield and selectivity (Scheme 2). 17 Under these conditions, the major side-product is the ring-opened ketone resulting from protodemetalation of the Pd homoenolate prior to β-hydride elimination. 1-Substituted and 1,2- disubstituted cyclopropyl alcohols were ring-opened using this methodology.…”

Section: Metal-catalyzed β-Carbon Elimination (Metal Homoenolates)mentioning

confidence: 99%

“…22 In 2018, Dai and co-workers reported a Cu-catalyzed γbutyrolactone and δ-ketoester synthesis from cyclopropyl alcohols, which is thought to proceed via enone intermediates (Scheme 5a). 23 Under Cu catalysis, cyclopropyl alcohols (16) can be treated with α-haloesters (17) to arrive at the γbutyrolactone (18). This reaction is thought to begin by the formation of either a Cu(II) homoenolate (19) or β-keto radical (20) from the cyclopropyl alcohol (16).…”

Section: Metal-catalyzed β-Carbon Elimination (Metal Homoenolates)mentioning

confidence: 99%

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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“…6 Two catalytic cycles depending on the Pd oxidation state have been proposed (Scheme 1, paths a 7 and b). 8 Reaction of palladium with the O-H bond leads to either 1 A or 1 B. Subsequent cleavage of the C-C bond provides 1 C and 1 D, respectively.…”

Section: Conversion To Enonesmentioning

confidence: 99%

Pd-catalyzed reactions of cyclopropanols, cyclobutanols and cyclobutenols

Bras

Мuzart

2020

Tetrahedron

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The exploitation of the ring strain of cyclopropanols, cyclobutanols and cyclobutenols has led to a variety of Pd-catalyzed reactions, especially when the ring is substituted with other functions. Cross-coupling and domino reactions have also been reported. The present review gathers together the literature results with special attention to the procedures. Proposed mechanisms are described with, in some cases, personal comments.

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ChemInform Abstract: Pd‐Catalyzed Ring Opening of Cyclopropanols.

Abstract: 2000 cyclopropane derivatives cyclopropane derivatives Q 0021 -084Pd-Catalyzed Ring Opening of Cyclopropanols.-In the presence of catalytic Pd-compounds, 1-substituted cyclopropanols (I) and (IV) undergo a ring opening to enones (II) and (V) in good yields.-(OKUMOTO,

Cited by 12 publications

References 1 publication

Transition-Metal-Catalyzed Rearrangements of Small Cycloalkanes: Regioselectivity Trends in β-Carbon Elimination Reactions

Transition-Metal-Catalyzed Rearrangements of Small Cycloalkanes: Regioselectivity Trends in β-Carbon Elimination Reactions

Selective Carbon–Carbon Bond Cleavage of Cyclopropanols

Pd-catalyzed reactions of cyclopropanols, cyclobutanols and cyclobutenols

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