General Ring‐Closing Metathesis

Hanson, Paul R.; Maitra, Soma; Chegondi, Rambabu; Markley, Jana L.

doi:10.1002/9783527674107.ch15

Cited by 15 publications

(8 citation statements)

References 243 publications

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“…With introduction of the new generations of highly active and chemoselective Ru metathesis catalysts endowed with high tolerance towards many functionalities and good stability in the presence of air, moisture and various solvents, including water-containing systems [231,232,233,234,235,236,237,238,239], the diversification of metathesis reactions experienced a strong impetus [240,241,242,243,244,245]. Among metathesis reactions, cross-metathesis (CM) [246,247,248,249] and ring-closing metathesis (RCM) [250,251,252,253,254] have become the most encountered strategies for the synthesis of linear and branched, or carbocyclic and heterocyclic compounds. Ru-catalyzed enyne metathesis (EYRCM) provided an elegant and productive way to obtain small, medium and large cyclic molecules [255].…”

Section: Ruthenium Complexes In Catalysismentioning

confidence: 99%

Editorial of Special Issue Ruthenium Complex: The Expanding Chemistry of the Ruthenium Complexes

Drăguţan

Demonceau

2015

Molecules

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Section: Ruthenium Complexes In Catalysismentioning

confidence: 99%

Editorial of Special Issue Ruthenium Complex: The Expanding Chemistry of the Ruthenium Complexes

Drăguţan

Demonceau

2015

Molecules

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“…Among the plethora of metathetic reactions of unsaturated compounds, e.g., alkene and enyne cross metathesis (CM [1] and EYCM [2][3][4]), alkene and enyne ring-closing metathesis (RCM and RCEYM) [5,6], ring-opening metathetic polymerization (ROMP) [7], etc., the CM and RCM are the most popular in organic synthesis [8]. Furthermore, the reactions of substrates containing three or more multiple bonds attracted special attention due to the applications in tandem metathesis processes Scheme 2: Beneficial effect of ethene atmosphere.…”

Section: Introductionmentioning

confidence: 99%

Ring-closing metathesis of prochiral oxaenediynes to racemic 4-alkenyl-2-alkynyl-3,6-dihydro-2H-pyrans

Kolaříková

Rybáčková

Svoboda

et al. 2020

Beilstein J. Org. Chem.

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The prochiral 4-(allyloxy)hepta-1,6-diynes, optionally modified in the positions 1 and 7 with an alkyl or ester group, undergo a chemoselective ring-closing enyne metathesis yielding racemic 4-alkenyl-2-alkynyl-3,6-dihydro-2H-pyrans. Among the catalysts tested, Grubbs 1st generation precatalyst in the presence of ethene (Mori conditions) gave superior results compared to the more stable Grubbs or Hoveyda–Grubbs 2nd generation precatalysts. This is probably caused by a suppression of the subsequent side-reactions of the enyne metathesis product with ethene. On the other hand, the 2nd generation precatalysts gave better yields in the absence of ethene. The metathesis products, containing both a triple bond and a conjugated system, can be successfully orthogonally modified. For example, the metathesis product of 5-(allyloxy)nona-2,7-diyne reacted chemo- and stereoselectively in a Diels–Alder reaction with N-phenylmaleimide affording the tricyclic products as a mixture of two separable diastereoisomers, the configuration of which was estimated by DFT computations. The reported enediyne metathesis paves the way to the enantioselective enyne metathesis yielding chiral building blocks for compounds with potential biological activity, e.g., norsalvinorin or cacospongionolide B.

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“…Among the plethora of metathetic reactions of unsaturated compounds, e.g. alkene and enyne cross metathesis (CM [1] and EYCM [2][3][4]), alkene and enyne ring-closing metathesis (RCM and RCEYM) [5], ring-opening metathetic polymerization (ROMP) [6], etc., CM and RCM are most popular in organic synthesis. Furthermore, reactions of substrates containing three or more multiple bonds attracted special attention due to applications in tandem metathesis processes [7][8] or stereodiscriminating enantioselective ring-closing metathetic reactions [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

Ring closing metathesis of prochiral oxaenediynes to racemic 4-alkenyl-2-alkynyl-3,6-dihydro-2H-pyrans

Kolaříková¹,

Rybáčková²,

Svoboda³

et al. 2020

Preprint

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Prochiral 4-(allyloxy)hepta-1,6-diynes, optionally modified in the positions 1 and 7 with an alkyl or ester group, undergo chemoselective ring closing enyne metathesis yielding racemic 4-alkenyl-2-alkynyl-3,6-dihydro-2H-pyrans. Among the catalysts tested, Grubbs 1st generation precatalyst in the presence of ethene (Mori conditions) gave superior results compared to more stable Grubbs or Hoveyda-Grubbs 2nd generation precatalysts. This is probably caused by suppression of subsequent side-reactions of the enyne metathesis product with ethene. On the other hand, 2nd generation precatalysts gave better yields in the absence of ethene. The metathesis products, containing both triple bond and conjugated system, can be successfully orthogonally modified. For example, metathesis product of 5-(allyloxy)nona-2,7-diyne reacted chemo- and stereoselectively by Diels-Alder reaction with N-phenylmaleimide affording tricyclic products as the mixture of two separable diastereoisomers, the configuration of which was estimated by DFT computations. The reported enediyne metathesis paves the way to enantioselective enyne metathesis yielding chiral building blocks for compounds with potential biological activity, e.g. norsalvinorin or cacospongionolide B.

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General Ring‐Closing Metathesis

Cited by 15 publications

References 243 publications

Editorial of Special Issue Ruthenium Complex: The Expanding Chemistry of the Ruthenium Complexes

Editorial of Special Issue Ruthenium Complex: The Expanding Chemistry of the Ruthenium Complexes

Ring-closing metathesis of prochiral oxaenediynes to racemic 4-alkenyl-2-alkynyl-3,6-dihydro-2H-pyrans

Ring closing metathesis of prochiral oxaenediynes to racemic 4-alkenyl-2-alkynyl-3,6-dihydro-2H-pyrans

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