Ruthenium Catalyzed Enyne Metathesis

Kinoshita, Atsushi; Mori, Miwako

doi:10.1055/s-1994-34973

Cited by 194 publications

(104 citation statements)

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“…After describing heterocycle synthesis using early transition metal Fischer carbenes, Mori and coworkers employed first Grubbs carbene, the vinyl carbene complex 5 for ring-closing metathesis (eq 9). [16] This accentuated the adaptability of the catalytic reaction to molecules with organic functional groups, which was apparent from Grubbs' work in the development of this catalyst. [6,17,18] In fact, Mori's report is the first methodology study of ring-closing enyne metathesis (RCEYM) showing a range of enynes that gave the metathesis.…”

Section: Enyne Metathesismentioning

confidence: 99%

“…[3] (12) (13) (14) In early reports on the intramolecular, ring-closing metathesis, internal alkynes were used with great success. [16] After the Blechert report, synthetic applications turned to intermolecular metathesis, and here the benefits of internal alkynes were overshadowed by the problem of poor regiocontrol. In the intermolecular enyne metathesis, the lack of a constraining device (i.e.…”

Section: Enyne Metathesismentioning

confidence: 99%

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Ruthenium vinyl carbene intermediates in enyne metathesis

Diver

2007

Coordination Chemistry Reviews

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This review provides an overview of ruthenium vinyl carbene reactivity as it relates to enyne metathesis. Methods for the synthesis of metathesis-active and metathesis-inactive complexes are also summarized. Some of the early hypotheses about vinyl carbene intermediates in enyne metatheses were tested in the arena of synthetic chemistry and subsequently led to mechanistic studies. In these two areas, studies from the author's labs are described. There are still many unresolved questions in enyne metathesis that trace back to vinyl carbene reactivity. Hopefully this review will stimulate further investigation into vinyl carbene reactivity which should further refine our understanding of catalytic enyne metathesis.

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Section: Enyne Metathesismentioning

confidence: 99%

Section: Enyne Metathesismentioning

confidence: 99%

Ruthenium vinyl carbene intermediates in enyne metathesis

Diver

2007

Coordination Chemistry Reviews

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“…To this solution were added Et 3 N (1.9 mL, 13.87 mmol) and NsCl (1.54 g, 6.93 mmol) at 0 8C, and the solution was stirred for 1.5 h. Saturated NH 4 Cl solution was added, and the mixture was extracted with AcOEt. The organic phase was washed with saturated NaCl solution, dried over MgSO 4 , and concentrated.…”

Section: Methyl 4-(2-nitrobenzenesulfonylamino)-cyclopent-2-enecarboxmentioning

confidence: 99%

“…[3] We have already reported various enyne metathesis reactions catalyzed by ruthenium carbene complex 1a or 1b, [4] including the effect of ethylene for the RCM [4c] and CM (cross metathesis) of alkynes, which is an effective synthetic method for 2,3-disubstituted-1,3-dienes. [4b,d,e] Recently, the ROM-RCM [5] of cycloalkene-ynes under an ethylene atmosphere was reported by our group (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Pyrrolizidine, Indolizidine, and Quinolizidine Derivatives Using Ruthenium‐Catalyzed Ring‐Opening Metathesis and Ring‐Closing Metathesis of Cycloalkene‐ynes

et al. 2007

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Ring-opening metathesis and ring-closing metathesis (ROM-RCM) of a cyclopentene-yne having an ester moiety was demonstrated using firstand second-generation Grubbs catalysts. When the reaction of cycloalkene-yne was carried out in the presence of 5 mol % of a ruthenium carbene complex under an ethylene atmosphere at room temperature, ROM-RCM proceeded smoothly to give a pyrrolidine derivative in good yield, which could be converted to a pyrrolizidine derivative. Furthermore, ROM-RCM of azabicycloA C H T U N G T R E N N U N G [2.2.1]heptene-ynes using the second-generation Grubbs catalyst was investigated. When an azabicycloheptene derivative was exposed to a catalytic amount of a ruthenium carbene complex, pyrrolizidine and indolizidine derivatives were obtained in good yields. The distribution of these products depends on the substituents on the alkyne. When azabicycloA C H T U N G T R E N N U N G [2.2.1]heptene-ynes bearing large substituents on the alkyne were treated with ruthenium catalyst 1b, a pyrrolizidine derivative was obtained as the major product. ROM-RCM of azabicycloA C H T U N G T R E N N U N G [2.2.2]octene-ynes with 1b afforded quinolizidine derivative 20, although the yield was moderate.

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“…As an extension of the latter studies, we report here that by replacing the diene moieties in B by enynes (type D), a variety of other transition metal mediated transformations, such as enyne metathesis [8] and Pauson-Khand cycloaddition, [9] can be performed. The enyne metathesis reaction gives access to spiroacetals with a 1,3-diene moiety (e.g.…”

Section: Synthesis Of Highly Functionalised Spiroacetals With the Rinmentioning

confidence: 99%