Ruthenium catalyzed reconstitutive condensation. Application to functionalized steroid side chains.

Trust, Barry M.; Kulawiec, Robert J.; Hammes, Alf

doi:10.1016/s0040-4039(00)61626-x

Cited by 49 publications

(22 citation statements)

References 30 publications

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“…[31] The terminal alkyne substrate 44 was prepared by Corey-Fuchs homologation of the commercially available 3-oxopregn-4-ene-20β-carboxaldehyde (43). [32] In this transformation, the enone present in the substrate was effectively protected from side reactions by conversion to the corresponding enolate prior to the reaction.…”

Section: Intramolecularmentioning

confidence: 99%

Metal Vinylidenes as Catalytic Species in Organic Reactions

Trost

McClory

2008

Chemistry An Asian Journal

189

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Organic vinylidene species have found limited use in organic synthesis due to their inaccessibility. In contrast, metal vinylidenes are much more stable, and may be readily accessed through transition metal activation of terminal alkynes. These electrophilic species may be trapped by a number of nucleophiles. Additionally, metal vinylidenes can participate in pericyclic reactions and processes involving migration of a metal ligand to the vinylidene species. This review addresses the reactions and applications of metal vinylidenes in organic synthesis.

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Section: Intramolecularmentioning

confidence: 99%

Metal Vinylidenes as Catalytic Species in Organic Reactions

Trost

McClory

2008

Chemistry An Asian Journal

189

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“…[24] Moreover, it lends itself well to synthesis. For example rosefuran (22), the essence of rose oil, was synthesized in 23 % overall yield in a concise six-step sequence starting with acetylene 19 and allylic alcohol 20.…”

Section: Reviewsmentioning

confidence: 99%

“…[25] Later, a second-generation catalyst system with In(OTf) 3 as a halophilic cocatalyst allowed a decrease in the amounts of allylic alcohol required for complete conversion into a nearly equimolar ratio with respect to the alkyne coupling partner. [24,26] The role of the cocatalyst is probably to remove chloride ion, thus generating a coordinatively more unsaturated Ru cation.…”

Section: Reviewsmentioning

confidence: 99%

Ruthenium‐Catalyzed Reactions—A Treasure Trove of Atom‐Economic Transformations

2005

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The demand for new chemicals spanning the fields of health care to materials science combined with the pressure to produce these substances in an environmentally benign fashion pose great challenges to the synthetic chemical community. The maximization of synthetic efficiency by the conversion of simple building blocks into complex targets remains a fundamental goal. In this context, ruthenium complexes catalyze a number of non-metathesis conversions and allow the rapid assembly of complex molecules with high selectivity and atom economy. These complexes often exhibit unusual reactivity. Careful consideration of the mechanistic underpinnings of the transformations can lead to the design of new reactions and the discovery of new reactivity.

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“…[24] Mithilfe dieser Reaktion wurde z. B. Rosenfuran (22), die Essenz von Rosenöl, aus dem Alkin 19 und dem Allylalkohol 20 in einer kurzen, sechsstufigen Sequenz in 23 % Gesamtausbeute synthetisiert.…”

Section: Aufsätzeunclassified

“…[25] Später konnte mithilfe einer zweiten Generation von Katalysatorsystemen mit In(OTf) 3 als halogenophilem Cokatalysator die Allylalkoholmenge, die zur vollständigen Umsetzung benötigt wurde, bis auf ein fast äquimolares Verhält-nis zum Alkin-Kupplungspartner verringert werden. [24,26] Wahrscheinlich entfernt der Cokatalysator das Chloridion und erzeugt so ein koordinativ weniger gesättigtes Ruthenium-Kation.…”

Section: Aufsätzeunclassified

Ruthenium‐katalysierte Reaktionen – eine Schatzkiste für atomökonomische Umwandlungen

2005

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Der stetige Bedarf an neuen Chemikalien bei gleichzeitiger Forderung nach umweltfreundlichen Herstellungsmethoden stellt an Synthesechemiker große Anforderungen. Die Maximierung der Syntheseeffizienz durch die Umwandlung einfacher Bausteine in komplexe Zielmoleküle bleibt daher eine grundlegende Aufgabe. In diesem Zusammenhang ist die Verwendung von Ruthenium‐Komplexen als Katalysatoren für mehrere nichtmetathetische Umwandlungen ein vielversprechender Ansatz, denn diese Komplexe ermöglichen den schnellen Aufbau komplexer Moleküle mit hoher Selektivität und Atomökonomie. Zudem zeigen sie häufig ungewöhnliche Reaktivität, und durch das sorgfältige Studium der zugrundeliegenden Mechanismen können neue Reaktionen entwickelt und neue Reaktivitäten entdeckt werden.

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Ruthenium catalyzed reconstitutive condensation. Application to functionalized steroid side chains.

Cited by 49 publications

References 30 publications

Metal Vinylidenes as Catalytic Species in Organic Reactions

Metal Vinylidenes as Catalytic Species in Organic Reactions

Ruthenium‐Catalyzed Reactions—A Treasure Trove of Atom‐Economic Transformations

Ruthenium‐katalysierte Reaktionen – eine Schatzkiste für atomökonomische Umwandlungen

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