Concise Syntheses of Insect Pheromones Using <i>Z</i>‐Selective Cross Metathesis

Herbert, Myles B.; Marx, Vanessa M.; Pederson, Richard L.; Grubbs, Robert H.

doi:10.1002/anie.201206079

Cited by 97 publications

(48 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…116 Various cross partners can be used, including vinyl–B(pin) and allylic acetals (Scheme 39b). 117 The corresponding ROCM processes have been reported as well, including those with an enantiomerically pure sample of Ru–11a , which has been obtained in three steps and after a chromatographic separation in ∼30% overall yield.…”

Section: Other Z-selective Ru Catalysts For Ommentioning

confidence: 99%

Evolution of Catalytic Stereoselective Olefin Metathesis: From Ancillary Transformation to Purveyor of Stereochemical Identity

2014

View full text Add to dashboard Cite

There have been numerous significant advances in catalytic olefin metathesis (OM) during the past two decades. Such progress has transformed this important set of reactions to strategically pivotal processes that generate stereochemical identity while delivering molecules that cannot be easily prepared by alternative routes. In this Perspective, an analysis of the origin of the inception of bidentate benzylidene ligands for Ru-based OM catalysts is first presented. This is followed by an overview of the intellectual basis that culminated in the development of Mo-based diolates and stereogenic-at-Ru complexes for enantioselective OM. The principles accrued from the study of the latter Ru carbenes and Mo alkylidenes and utilized in the design of stereogenic-at-Mo, -W, and -Ru species applicable to enantioselective and Z-selective OM are then discussed. The influence of the recently introduced catalytic OM protocols on the design of synthesis routes leading to complex organic molecules is probed. The impact of a better understanding of the mechanistic nuances of OM toward the discovery of stereoselective catalysts is reviewed as well.

show abstract

Section: Other Z-selective Ru Catalysts For Ommentioning

confidence: 99%

Evolution of Catalytic Stereoselective Olefin Metathesis: From Ancillary Transformation to Purveyor of Stereochemical Identity

2014

View full text Add to dashboard Cite

show abstract

“…13 Herein, we disclose the first report of Z -selective macrocyclic RCM using a ruthenium-based catalyst system ( 2 ), applicable to a broad range of ring sizes and functional groups. Additionally, we report the first instance of Z -selective ethenolysis of macrocycles, resulting in pure E -macrocycles from an E / Z -mixture, using the same catalyst system ( 2 ).…”

mentioning

confidence: 99%

Stereoselective Access to Z and E Macrocycles by Ruthenium-Catalyzed Z-Selective Ring-Closing Metathesis and Ethenolysis

et al. 2012

Self Cite

View full text Add to dashboard Cite

The first report of Z-selective macrocyclizations using a ruthenium-based metathesis catalyst is described. Selectivity for Z-macrocycles is consistently high for a diverse set of substrates with a variety of functional groups and ring sizes. The same catalyst was also employed for the Z-selective ethenolysis of a mixture of E and Z macrocycles, providing the pure E-isomer. Notably, only an atmospheric pressure of ethylene was required. These methodologies were successfully applied to the construction of several olfactory macrocycles, as well as the formal total synthesis of the cytotoxic alkaloid motuporamine C.

show abstract

“…Seemingly cruel to the insects targeted, this method is much less toxic to other species, which can be affected by the use of pesticides. Grubbs and coworkers have utilized 6 to aid in the synthesis of nine pheromones from the lepidopteran order of insects [101]. Many of the pheromones from this order of insects contain or can utilize a Z-olefin in the synthesis [102], thus making 6 a good candidate to streamline the synthesis of these desired compounds.…”

Section: Stereoselective Olefin Metathesis In Synthetic Applicationsmentioning

confidence: 99%

Recent Advancements in Stereoselective Olefin Metathesis Using Ruthenium Catalysts

2017

Self Cite

View full text Add to dashboard Cite

Olefin metathesis is a prevailing method for the construction of organic molecules. Recent advancements in olefin metathesis have focused on stereoselective transformations. Ruthenium olefin metathesis catalysts have had a particularly pronounced impact in the area of stereoselective olefin metathesis. The development of three categories of Z-selective olefin metathesis catalysts has made Z-olefins easily accessible to both laboratory and industrial chemists. Further design enhancements to asymmetric olefin metathesis catalysts have streamlined the construction of complex molecules. The understanding gained in these areas has extended to the employment of ruthenium catalysts to stereoretentive olefin metathesis, the first example of a kinetically E-selective process. These advancements, as well as synthetic applications of the newly developed catalysts, are discussed.

show abstract

Concise Syntheses of Insect Pheromones Using Z‐Selective Cross Metathesis

Cited by 97 publications

References 34 publications

Evolution of Catalytic Stereoselective Olefin Metathesis: From Ancillary Transformation to Purveyor of Stereochemical Identity

Evolution of Catalytic Stereoselective Olefin Metathesis: From Ancillary Transformation to Purveyor of Stereochemical Identity

Stereoselective Access to Z and E Macrocycles by Ruthenium-Catalyzed Z-Selective Ring-Closing Metathesis and Ethenolysis

Recent Advancements in Stereoselective Olefin Metathesis Using Ruthenium Catalysts

Contact Info

Product

Resources

About