Ring-closing metathesis

Definition: A joining reaction in which two carbon-carbon double bonds in the same molecule are redistributed to give a cycloalkene. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of a low-MW alkene.

ID: RXNO:0000245

Synonyms:

More about the RSC Name Reaction Ontology (RXNO)

Articles referencing this term

Conjugated imines and iminium salts as versatile acceptors of nucleophiles
Makoto Shimizu, Iwao Hachiya and Isao Mizota, Chem. Commun., 2009 , 874
DOI: 10.1039/b814930e

α-Zirconium phosphonates: versatile supports for N-heterocyclic carbenes
Simona Chessa, Nigel J. Clayden, Manfred Bochmann and Joseph A. Wright, Chem. Commun., 2009 , 797
DOI: 10.1039/b821301a

Polycyclic alkaloids via transannular Mannich reactions
Paulo Vital, Masood Hosseini, M. Sundaram Shanmugham, Charlotte H. Gotfredsen, Pernille Harris and David Tanner, Chem. Commun., 2009 , 1888
DOI: 10.1039/b822955d

Solid-phase based total synthesis of Jasplakinolide by ring-closing metathesis
René Tannert, Tai-Shan Hu, Hans-Dieter Arndt and Herbert Waldmann, Chem. Commun., 2009 , 1493
DOI: 10.1039/b900342h

Combining two-directional synthesis and tandem reactions: new access to 3,5-disubstituted pyrrolizidines and first total synthesis of alkaloid cis-223B
Jean-Chistophe Legeay, William Lewis and Robert A. Stockman, Chem. Commun., 2009 , 2207
DOI: 10.1039/b900451c

The first total synthesis of (±)-apparicine
M.-Lluïsa Bennasar, Ester Zulaica, Daniel Solé and Sandra Alonso, Chem. Commun., 2009 , 3372
DOI: 10.1039/b903577j

An enantiopure cyclophane-type imidazole with no central but planar chirality
Yasuhiro Ishida, Eriko Iwasa, Yuki Matsuoka, Hiroyuki Miyauchi and Kazuhiko Saigo, Chem. Commun., 2009 , 3401
DOI: 10.1039/b904059e

Enantioselective total synthesis of the indole alkaloid 16-episilicine
Mercedes Amat, Begoña Checa, Núria Llor, Elies Molins and Joan Bosch, Chem. Commun., 2009 , 2935
DOI: 10.1039/b904521j

Novel epothilone lactones by an unusual diversion of the Grubbs' metathesis reaction
Qiao-Hong Chen, Thota Ganesh, Yi Jiang, Abhijit Banerjee, Shubhada Sharma, Susan Bane, James P. Snyder and David G. I. Kingston, Chem. Commun., 2010 , 46 , 2019
DOI: 10.1039/b926174e

Asymmetric synthesis of bis-tetrahydrofuran cores in annonaceous acetogenins
Chia-Hsiu Chen, Ting-Chun Kuan, Ke-Jhen Lu and Duen-Ren Hou, Org. Biomol. Chem., 2010 , 8 , 3624
DOI: 10.1039/c004672h

A three-step tandem process for the synthesis of bicyclic γ-lactams
Fiona I. McGonagle, Lindsay Brown, Andrew Cooke and Andrew Sutherland, Org. Biomol. Chem., 2010 , 8 , 3418
DOI: 10.1039/c004695g

De novo synthesis of polyhydroxyl aminocyclohexanes
Anobick Sar, Sergey Lindeman and William A. Donaldson, Org. Biomol. Chem., 2010 , 8 , 3908
DOI: 10.1039/c004730a

Stereocontrolled synthesis of quaternary cyclopropyl esters
Christopher D. Bray and Fabrizio Minicone, Chem. Commun., 2010 , 46 , 5867
DOI: 10.1039/c0cc01333a

Total synthesis of (±)-Vertine with Z-selective RCM as a key step
Laetitia Chausset-Boissarie, Roman Àrvai, Graham R. Cumming, Céline Besnard and E. Peter Kündig, Chem. Commun., 2010 , 46 , 6264
DOI: 10.1039/c0cc01885f

Synthetic studies on the mycolactone core
Kwang-Seuk Ko, Matthew D. Alexander, Shaun D. Fontaine, James E. Biggs-Houck, James J. La Clair and Michael D. Burkart, Org. Biomol. Chem., 2010 , 8 , 5159
DOI: 10.1039/c0ob00540a

Total synthesis of all (−)-agelastatin alkaloids
Mohammad Movassaghi, Dustin S. Siegel and Sunkyu Han, Chem. Sci., 2010 , 1 , 561
DOI: 10.1039/c0sc00351d