Construction of Carbocycles from Methylenecyclopropanes

Cao, Huaqiang; Chen, Fenglin; Su, Chenliang; Yu, Lei

doi:10.1002/adsc.201900615

Cited by 40 publications

(14 citation statements)

References 206 publications

(211 reference statements)

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“…The strain release derived from cyclopropane expansion has been extensively used to thermodynamically favor the construction of 4-membered cycles. ,,, Under gold(I) catalysis, a wide range of cyclopropane-embedded frameworks can undergo ring expansion to efficiently assemble substituted cyclobutanes. ,,,, …”

Section: Construction Of 4-membered Rings Catalyzed By Goldmentioning

confidence: 99%

“…7 , 8 , 41 , 646 Under gold(I) catalysis, a wide range of cyclopropane-embedded frameworks can undergo ring expansion to efficiently assemble substituted cyclobutanes. 41 , 644 , 645 , 647 , 648 …”

Section: Construction Of 4-membered Rings Catalyzed By Goldmentioning

confidence: 99%

“…7,8,41,646 Under gold(I) catalysis, a wide range of cyclopropane-embedded frameworks can undergo ring expansion to efficiently assemble substituted cyclobutanes. 41,644,645,647,648 3. Interestingly, the diastereoselectivity varied according to the gold(I) catalyst employed.…”

Section: Synthesis Of Cyclobutanesmentioning

confidence: 99%

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Gold-Catalyzed Synthesis of Small Rings

et al. 2020

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Three- and four-membered rings, widespread motifs in nature and medicinal chemistry, have fascinated chemists ever since their discovery. However, due to energetic considerations, small rings are often difficult to assemble. In this regard, homogeneous gold catalysis has emerged as a powerful tool to construct these highly strained carbocycles. This review aims to provide a comprehensive summary of all the major advances and discoveries made in the gold-catalyzed synthesis of cyclopropanes, cyclopropenes, cyclobutanes, cyclobutenes, and their corresponding heterocyclic or heterosubstituted analogs.

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Section: Construction Of 4-membered Rings Catalyzed By Goldmentioning

confidence: 99%

Section: Construction Of 4-membered Rings Catalyzed By Goldmentioning

confidence: 99%

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Gold-Catalyzed Synthesis of Small Rings

et al. 2020

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“…Finally, the last three sections will discuss special classes of cyclopropanes substituted with C–C unsaturations: Vinylcyclopropanes (section ), alkylidenecyclopropanes (section ), and vinylidenecyclopropanes (section ). The presence of the more reactive π systems opens the way for other types of transition-metal-based activations, which has been described in dedicated reviews, − none of them specific to asymmetric transformations however. Cyclopropenes have been only rarely used in asymmetric ring-opening transformations and are not covered in this review …”

Section: Introductionmentioning

confidence: 99%

Catalytic Enantioselective Ring-Opening Reactions of Cyclopropanes

2020

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This review describes the development of enantioselective methods for the ring opening of cyclopropanes. Both approaches based on the reaction of nonchiral cyclopropanes and (dynamic) kinetic resolutions and asymmetric transformations of chiral substrates are presented. The review is organized according to substrate classes, starting by the more mature field of donor−acceptor cyclopropanes. Emerging methods for enantioselective ring opening of acceptor-or donor-only cyclopropanes are then presented. The last part of the review describes the ring opening of more reactive three-membered rings substituted with unsaturations with a particular focus on vinylcyclopropanes, alkylidenecyclopropanes, and vinylidenecyclopropanes. In the last two decades, the field has grown from a proof of concept stage to a broad range of methods for accessing enantioenriched building blocks, and further extensive developments can be expected in the future.

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“… 7 The reported borocarbonylation of alkenes was limited to styrenes and did not allow for regioselectivity control. 7 b Thus, variants involving methylenecyclopropanes 8 are particularly attractive because of the potential to control the formation of various boryl ketones. As depicted in Fig.…”

Section: Introductionmentioning

confidence: 99%