Makrocyclische Cyclopropene durch hochenantioselektive intramolekulare Additionen von Metallcarbenen an Alkine

Doyle, Michael P.; Ene, Doina G.; Peterson, Courtney M.; Lynch, Vince

doi:10.1002/(sici)1521-3757(19990301)111:5<722::aid-ange722>3.0.co;2-r

Angewandte Chemie

1999

DOI: 10.1002/(sici)1521-3757(19990301)111:5<722::aid-ange722>3.0.co;2-r

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Makrocyclische Cyclopropene durch hochenantioselektive intramolekulare Additionen von Metallcarbenen an Alkine

Michael P. Doyle

Doina G. Ene

Courtney M. Peterson

et al.

Abstract: Durch die intramolekulare Addition einer Diazoestergruppe an eine Dreifachbindung werden in Gegenwart von chiralen Dirhodium(II)‐carboxamidat‐Katalysatoren makrocyclische Lactone mit anelliertem Cyclopropenring erhalten [Gl. (a)]. Diese effiziente Reaktion zeichnet sich durch hohe Enantioselektivitäten (bis zu 98 % ee) sowie hohe Chemoselektivitäten aus.

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Cited by 10 publications

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Synthetic Applications of Vinyl Ruthenium Carbenes Derived from Diazoalkanes and Alkynes

Dey

Sarkar

2017

Adv Synth Catal

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Ruthenium‐catalyzed C–C bond forming reactions between diazoalkanes and alkynes have gained much attention in recent years due to their unique ways for the formation of various synthetic scaffolds via an electrophilic vinyl ruthenium carbene intermediate. These 16‐electron species are isoelectronic with the Grubbs type ruthenium‐benzylidene catalyst, but their structural geometry and ligand liability make them more innovative in catalytic reactions. Recent advances in this field with respect to vinyl ruthenium carbenes and their coupling partners, thus leading to a step‐economical access to versatile molecular architectures, are discussed herein in a sustainable manner.

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Synthetic Applications of Vinyl Ruthenium Carbenes Derived from Diazoalkanes and Alkynes

Dey

Sarkar

2017

Adv Synth Catal

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Dirhodium(II)‐Catalyzed Cyclopropanation of Alkyne‐Containing α‐Diazoacetates for the Synthesis of Cycloalkynes

Zeng

Zhou

et al. 2020

Adv Synth Catal

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Enantiomerenangereicherte Cyclopropene: vielseitige Bausteine in der asymmetrischen Synthese

2007

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Enantiomerenangereicherte Cyclopropenderivate, die kleinstmöglichen ungesättigten Carbocyclen, sind von großem Interesse für die Synthese, da sie als vielseitige reaktive Bausteine eingesetzt werden können. Die Reaktivität rührt von der Ringspannung her, die durch Umsetzungen gemildert wird. Die Cyclopropenderivate können zu komplexeren chiralen Strukturen umgesetzt werden, wobei in diesem Aufsatz besonders die Herstellung von enantiomerenangereicherten Methylen‐ und Alkylidencyclopropanderivaten herausgehoben wird. Die einfache Verfügbarkeit chiraler Bausteine dieser Art bildet eine ausgezeichnete Grundlage für die Entdeckung neuartiger Reaktionen, die das Repertoire der organischen Synthese bereichern können.

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Makrocyclische Cyclopropene durch hochenantioselektive intramolekulare Additionen von Metallcarbenen an Alkine

Cited by 10 publications

References 18 publications

Synthetic Applications of Vinyl Ruthenium Carbenes Derived from Diazoalkanes and Alkynes

Synthetic Applications of Vinyl Ruthenium Carbenes Derived from Diazoalkanes and Alkynes

Dirhodium(II)‐Catalyzed Cyclopropanation of Alkyne‐Containing α‐Diazoacetates for the Synthesis of Cycloalkynes

Enantiomerenangereicherte Cyclopropene: vielseitige Bausteine in der asymmetrischen Synthese

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