An isomerization-ring-closing metathesis strategy for the synthesis of substituted benzofurans

Otterlo, Willem A. L. van; Morgans, Garreth L.; Madeley, Lee G.; Kuzvidza, Samuel; Moleele, Simon S.; Thornton, Natalie; Koning, Charles B. de

doi:10.1016/j.tet.2005.05.090

Cited by 97 publications

(49 citation statements)

References 57 publications

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“…(219)) [1058]. Double bond isomerization RCM sequences using two different ruthenium catalysts were described [1059,1060]. A domino-RCM was reported (Eq.…”

Section: Metathesis Reactionsmentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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“…(219)) [1058]. Double bond isomerization RCM sequences using two different ruthenium catalysts were described [1059,1060]. A domino-RCM was reported (Eq.…”

Section: Metathesis Reactionsmentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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“…On the other hand, van Otterlo and coworkers utilized an isomerization/RCM strategy for the synthesis of substituted benzofurans (03TL6483,05T7746). Isomerization of the allyl groups in precursor 38 was performed using a ruthenium complex 39 to form the aryl enol ethers 40; subsequent RCM with catalyst 3 then provided the desired benzofurans 37 in excellent yields (Scheme 11).…”

Section: Benzofurans Indoles and Benzimidazolesmentioning

confidence: 99%

Synthesis of Aromatic Heterocycles Using Ring-Closing Metathesis

Potukuchi

Colomer

Donohoe

2016

Advances in Heterocyclic Chemistry

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“…This underwent smooth RCM, and following hydrogenative debenzylation, target 30 was isolated in good yield. van Otterlo and co-workers have reported an alternative entry to metathesis precursors 32 via Ru-hydride-catalysed double isomerisation [45][46][47][48] of diallylated phenols 31 (Scheme 13c) [49,50]. RCM, using G2, provided a series of benzofurans (e.g.…”

Section: Synthesis Of Benzofused 5-ring Heteroaromatic Systems By Rcmmentioning

confidence: 99%

Synthesis of Heteroaromatic Compounds by Alkene and Enyne Metathesis

Race

Bower

2015

Topics in Heterocyclic Chemistry

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The development of robust and functional group tolerant metathesis catalysts has resulted in a rapid expansion of synthetic methodologies that employ this technology. In this chapter, alkene and enyne metathesis-based methodologies for the de novo construction of heteroaromatic compounds are discussed. These protocols capitalise upon the ability to generate complex olefinic products from the combination of two simpler precursors. Advancement to the heteroaromatic target can then be achieved either directly or after modification of the immediate metathesis product. Strategies that rely upon ring-closing alkene metathesis, ring-closing enyne metathesis and alkene cross-metathesis are outlined, along with applications in target-directed synthesis.

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An isomerization-ring-closing metathesis strategy for the synthesis of substituted benzofurans

Cited by 97 publications

References 57 publications

Transition metals in organic synthesis: Highlights for the year 2005

Transition metals in organic synthesis: Highlights for the year 2005

Synthesis of Aromatic Heterocycles Using Ring-Closing Metathesis

Synthesis of Heteroaromatic Compounds by Alkene and Enyne Metathesis

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