Selective Synthesis of Chiral Dioxabicyclo[4.4.0]decane and Dioxabicyclo[5.3.0]decane from 3,4-Bisallyloxy-but-1-yne Derivatives via Ruthenium-Catalyzed En-yn-ene Metathesis

Wu, Chang-Jung; Madhushaw, Reniguntala J.; Liu, Rai‐Shung

doi:10.1021/jo0301548

Cited by 38 publications

(7 citation statements)

References 32 publications

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“…[32] The results discussed above are related to previous reports describing a significant erosion in selectivity of double ring-closing metathesis reactions whenever ruthenium carbenes with an NHC ligand are used as catalysts. This is not limited to ring size-selectivity, [31,45] as in our example, but has also been observed in diastereoselective double RCM reactions. [46][47][48] However, the level of selectivity towards the formation of bis-dihydrofuran 10 with the first-generation catalyst A is quite remarkable.…”

Section: Regioselective Double Rcm: Fused Vs Dumbbelltype Bicyclic Ssupporting

confidence: 74%

Synthesis of Dihydrofurans and Dihydropyrans with Unsaturated Side Chains Based on Ring Size‐Selective Ring‐Closing Metathesis

Schmidt

Nave

2007

Adv Synth Catal

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Enantiomerically pure 1,5-hexadiene-3,4-diol, derived from d-mannitol in a few steps, may serve as a starting material for enantiopure dihydropyrans and dihydrofurans bearing an unsaturated side chain which is amenable for further synthetic transformations. The synthesis relies on a ring sizeselective ring-closing metathesis reaction of a triene. Most likely, a catalyst-directing effect of an allylic hydroxy group is responsible for the selectivity.

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Section: Regioselective Double Rcm: Fused Vs Dumbbelltype Bicyclic Ssupporting

confidence: 74%

Synthesis of Dihydrofurans and Dihydropyrans with Unsaturated Side Chains Based on Ring Size‐Selective Ring‐Closing Metathesis

Schmidt

Nave

2007

Adv Synth Catal

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“…Lui and co-workers have also investigated the dienyne ringclosing metathesis as a methodology leading to the formation of oxygen-containing bicyclic systems. 51 Among the substrates examined, dienyne 60 is of interest since numerous products are formed as a function of the catalyst used (Scheme 13). Both complexes Cat-1A and Cat-1C displayed good activity leading to the formation of dioxabicyclo[4.4.0]decane 61 as major product, resulting from an endo cyclization.…”

Section: Ring-closing Metathesis Of Enynesmentioning

confidence: 99%

Chemoselective olefin metathesis transformations mediated by ruthenium complexes

2010

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Over the past decade, ruthenium-mediated metathesis transformations, including polymerization reactions, cross-metathesis, ring-closing metathesis, enyne metathesis, ring-rearrangement metathesis, and also tandem processes, represent one of the most studied families of organic reactions. This has translated into the development of a large number of structurally diverse catalysts. Whereas most of these investigations are focused on determining catalytic performance, only rare examples of studies dealing with chemoselectivity have been reported to date. Usually, variations are observed in product conversions but rarely in product distributions. In this critical review, we provide an overview of the stereochemistry of newly formed C=C bonds either in ring-closing or cross-metathesis as a function of the catalyst structure. A discussion of disparities encountered in macrocyclisation reactions leading (or not) to the formation of dimeric products is also presented. Since distinctive metathesis products could be isolated as a function of the ligand borne by the ruthenium centre--phosphine or N-heterocyclic carbene in the dissymetrization of trienes, enyne metathesis and ring rearrangements, these topics are also discussed (72 references).

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“…Similarly, Liu et al reported a moderately group-selective tandem enyne RCM for the synthesis of small-sized fused bicycles (Scheme 13). [27] The dienynes cyclized to form similar ratios of products, consistently favoring the initial ring closure to the six-over five-membered ring regardless of the presence of substitution on the alkyne or the catalyst employed (1 a vs 2). The observed selectivity could arise from a ring closure rate difference during the initial five-and sixmembered ring formation.…”

Section: Group Differentiation Strategymentioning

confidence: 88%

Group‐Selective Ring‐Closing Enyne Metathesis

Maifeld

Lee

2005

Chemistry A European J

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The ring-closing metathesis (RCM) of dienynes represents a powerful methodology for the construction of mono- and bicyclic systems containing 1,3-diene functionality. Despite its synthetic potential, the utility of dienyne RCM is significantly reduced due to poor group selectivity. To circumvent this shortcoming, several strategies utilizing steric hindrance, electronic variation, relay metathesis and ring-closure kinetics have been implemented to exert control over the reaction pathways. This article highlights a variety of methods to achieve group-selective enyne RCM of dienynes.

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Selective Synthesis of Chiral Dioxabicyclo[4.4.0]decane and Dioxabicyclo[5.3.0]decane from 3,4-Bisallyloxy-but-1-yne Derivatives via Ruthenium-Catalyzed En-yn-ene Metathesis

Cited by 38 publications

References 32 publications

Synthesis of Dihydrofurans and Dihydropyrans with Unsaturated Side Chains Based on Ring Size‐Selective Ring‐Closing Metathesis

Synthesis of Dihydrofurans and Dihydropyrans with Unsaturated Side Chains Based on Ring Size‐Selective Ring‐Closing Metathesis

Chemoselective olefin metathesis transformations mediated by ruthenium complexes

Group‐Selective Ring‐Closing Enyne Metathesis

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