Modulation of Olefin Metathesis Reactions by Chelation

Scherbakow, Swetlana; Keller, Manfred; Bannwarth, Willi

doi:10.1002/ejoc.201402319

Eur J Org Chem

2014

DOI: 10.1002/ejoc.201402319

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Modulation of Olefin Metathesis Reactions by Chelation

Swetlana Scherbakow

Manfred Keller

Willi Bannwarth

Abstract: We describe the modulation of catalytic activities by adjacent chelating entities as a new and hitherto unknown principle. It is demonstrated for ring-closing metathesis (RCM) as well as for cross metathesis (CM) reactions. For this purpose, we have modified a Hoveyda-type metathesis catalyst by employing two different chelators. Complexation of the chela-

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Cited by 3 publications

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References 42 publications

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“…We were able to demonstrate that a complexation of the chelating unit in catalyst 8 (Fig. 3) had a significant positive effect on its efficiency in metathesis reactions [12].…”

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confidence: 79%

Modulation of Reactivities of Dienophiles for DielsAlder Reactions via Complexation of α,β‐Unsaturated Chelating Amides

Sterk

Bannwarth

2015

Helvetica Chimica Acta

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We describe the modulation of reactivities of dienophiles for DielsÀAlder reactions via a new principle based on chelating amides positioned adjacent to their C¼C bond. It is demonstrated for modified acrylic acid derivatives and related dienophiles with three different chelating entities. Complexation of the chelators leads to an intensified electron-withdrawing effect leading to an enhancement of reactivity in DielsÀAlder reactions depending on the complexed metal ion. The application of this new approach might be extended to other reactions with reacting entities adjacent to chelating amides.

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“…We were able to demonstrate that a complexation of the chelating unit in catalyst 8 (Fig. 3) had a significant positive effect on its efficiency in metathesis reactions [12].…”

mentioning

confidence: 79%

Modulation of Reactivities of Dienophiles for DielsAlder Reactions via Complexation of α,β‐Unsaturated Chelating Amides

Sterk

Bannwarth

2015

Helvetica Chimica Acta

Self Cite

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The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014

Herndon

2016

Coordination Chemistry Reviews

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Ring Rearrangement Metathesis in 7-Oxabicyclo[2.2.1]heptene (7-Oxanorbornene) Derivatives. Some Applications in Natural Product Chemistry

Roscales

Plumet

2017

Natural Product Communications

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Metathesis reactions is firmly established as a valuable synthetic tool in organic chemistry, clearly comparable with the venerable Diels-Alder and Wittig reactions and, more recently, with the metal-catalyzed cross-coupling reactions. Metathesis reactions can be considered as a fascinating synthetic methodology, allowing different variants regarding substrate (alkene and alkyne metathesis) and type of metathetical reactions. On the other hand, tandem metathesis reactions such Ring Rearrangement Metathesis (RRM) and the coupling of metathesis reaction with other reactions of alkenes such as Diels-Alder or Heck reactions, makes metathesis one of the most powerful and reliable synthetic procedure. In particular, Ring-Rearrangement Metathesis (RRM) refers to the combination of several metathesis transformations into a domino process such as ringopening metathesis (ROM)/ring-closing metathesis (RCM) and ROM-cross metathesis (CM) in a one-pot operation. RRM delivers complex frameworks that are difficult to assemble by conventional methods constitutingan atom economic process. RRM is applicable to mono-and polycyclic systems of varying ring sizes such as cyclopropene, cyclobutene, cyclopentene, cyclohexene, pyran systems, bicyclo[2.2.1]heptene derivatives, bicyclo[2.2.2]octene derivatives, bicyclo[3.2.1]octene derivatives and bicyclo[3.2.1]octene derivatives. In this review our attention has focused on the RRM reactions in 7-oxabicyclo[2.2.1]heptene derivatives and on their application in the synthesis of natural products or significant subunits of them.

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Modulation of Olefin Metathesis Reactions by Chelation

Cited by 3 publications

References 42 publications

Modulation of Reactivities of Dienophiles for DielsAlder Reactions via Complexation of α,β‐Unsaturated Chelating Amides

Modulation of Reactivities of Dienophiles for DielsAlder Reactions via Complexation of α,β‐Unsaturated Chelating Amides

The chemistry of the carbon-transition metal double and triple bond: Annual survey covering the year 2014

Ring Rearrangement Metathesis in 7-Oxabicyclo[2.2.1]heptene (7-Oxanorbornene) Derivatives. Some Applications in Natural Product Chemistry

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