Preparation of cyclic molecules bearing “strained” olefins using olefin metathesis

Collins, Shawn K.

doi:10.1016/j.jorganchem.2006.08.010

Cited by 29 publications

(12 citation statements)

References 54 publications

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“…RCM is for instance effective for the formation of C5‐macrocycles, but not for three‐ or four‐membered rings, as this is enthalpically highly unfavorable. In such reactions, ADMET proceeds almost exclusively . Moreover, at low diene concentrations RCM is favored, whereas the significance of ADMET increases at high monomer concentrations.…”

Section: Opportunities Of Heterogeneous Grubbs Catalystsmentioning

confidence: 99%

Opportunities of Immobilized Homogeneous Metathesis Complexes as Prominent Heterogeneous Catalysts

2016

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A plethora of strategies for immobilizing well‐defined metathesis catalysts on solid supports have been developed over the past decades. Whereas most reviews on classical heterogeneous metathesis catalyst designs mainly discuss covalent binding approaches, we here extended this topic with non‐covalent surface science methods, a research area that gained interest recently. Within this context, the main focus was set on the immobilization of ruthenium alkylidenes or so‐called Grubbs complexes, as these catalysts are known for their high activity, stability and commercial viability. Besides giving an overview of different immobilization strategies, the wide diversity of supported Grubbs catalysts also allows for discussing implications of attaching Grubbs catalysts that go beyond the traditional benefits of heterogeneous catalysis, such as easy catalyst separation. More specifically, this Review will summarize several unique opportunities of immobilized homogeneous catalysts in liquid‐phase metathesis transformations in terms of impact on activity, stability, and product selectivity, as to highlight the economic potential, but without ignoring possible shortcomings and limitations.

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Section: Opportunities Of Heterogeneous Grubbs Catalystsmentioning

confidence: 99%

Opportunities of Immobilized Homogeneous Metathesis Complexes as Prominent Heterogeneous Catalysts

2016

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“…For example, 3,3-diphenylcyclopropene has been well-known as an important starting material for the synthesis of valuable ruthenium-involved vinylalkylidene olefin metathesis catalyst via a ring-opening process . Since cyclopropenes cannot be formed by ring-closing metathesis (RCM) due to the highly strained energy, the ring-opening of the ruthenacyclobutane intermediate is irreversible. In such cases, cyclopropenes are more inclined to undergo ring-opening metathesis polymerization (ROMP) rather than ring-opening metathesis/cross-metathesis (ROM/CM).…”

mentioning

confidence: 99%

Ruthenium-Catalyzed Tandem Ring-Opening/Ring-Closing/Cross-Metathesis of 1,6-Cyclopropene-ynes and Olefins for the Construction of the 3-Pyrroline Skeleton

Zhu

Shi

2010

Org. Lett.

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“…With the key intermediates 2 in hand, the subsequent cyclization reactions to give estrone were accomplished (Scheme ). The C-ring closure by ring closing metathesis to the trans -hydrindene ring was investigated first using the racemic phosphonate 2a . RCM reaction using the Hoveyda-Grubbs II catalyst in toluene at 70 °C afforded trans -hydrindene rac - 12 in good yield.…”

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confidence: 99%

A Novel, Versatile D→BCD Steroid Construction Strategy, Illustrated by the Enantioselective Total Synthesis of Estrone

et al. 2010

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A general steroid synthesis is presented that relies on prior formation of three stereogenic centers (C8, C13, and C14) on a D ring template, followed by C- and B-ring cyclizations. The assembly of the key D ring template, achieved by a 3-component conjugate addition/alkylation process, allows introduction of structural variety as required. The method is illustrated by the total synthesis of estrone via a C-ring closing metathesis and a B-ring Heck cyclization.

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Preparation of cyclic molecules bearing “strained” olefins using olefin metathesis

Cited by 29 publications

References 54 publications

Opportunities of Immobilized Homogeneous Metathesis Complexes as Prominent Heterogeneous Catalysts

Opportunities of Immobilized Homogeneous Metathesis Complexes as Prominent Heterogeneous Catalysts

Ruthenium-Catalyzed Tandem Ring-Opening/Ring-Closing/Cross-Metathesis of 1,6-Cyclopropene-ynes and Olefins for the Construction of the 3-Pyrroline Skeleton

A Novel, Versatile D→BCD Steroid Construction Strategy, Illustrated by the Enantioselective Total Synthesis of Estrone

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