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Z-selectivity

Z-selective/Enantioselective ring-closing metathesis (RCM) is particularly important in the synthesis of biologically active products

For example, high Z-selectivity is required for the stereoselective transformation of the double-bonded intermediate towards the macrocyclic, anti-cancer natural product, Epothilone C.

Hoveyda, Schrock et al. Efficient and Selective Formation of Macrocyclic Disubstituted Z Alkenes by Ring‐Closing Metathesis (RCM) Reactions Catalyzed by Mo‐or W‐Based Monoaryloxide Pyrrolide (MAP) Complexes: Applications to Total Syntheses of Epilachnene, Yuzu Lactone, Ambrettolide, Epothilone C, and Nakadomarin Chem. Eur. J. 2013, 19, 2726 – 2740.

Further examples:

Efficient and Selective Formation of Macrocyclic Distributed Z Alkenes
The first broadly applicable set of protocols for efficient Z-selective formation of macrocyclic disubstituted alkenes through catalytic ring-closing metathesis (RCM) is described.
ChemViews, 23 January 2013

Z-Selective Olefin Metathesis Reactions Promoted by Tungsten Oxo Alkylidene Complexes
New homogeneous catalysts show highly promising activity and selectivity for a large variety of olefin metathesis reactions.
JACS, 8 January 2013

Molybdenum-Based Complexes with Two Aryloxides and a Pentafluoroimido Ligand
Catalysts for Efficient Z-Selective Synthesis of a Macrocyclic Trisubstituted Alkene by Ring-Closing Metathesis
Angewandte Chemie, 8 January 2013

Enol Ethers as Substrates for Efficient Z- and Enantioselective Ring-Opening/Cross-Metathesis Reactions Promoted by Stereogenic-at-Mo Complexes. Utility in Chemical Synthesis and Mechanistic Attributes
The first examples of catalytic enantioselective ring-opening/cross-metathesis (EROCM) reactions that involve enol ethers are reported. Catalytic EROCM of several oxa- and azabicycles, cyclobutenes and a cyclopropene with an alkyl- or aryl-substituted enol ether proceed readily in the presence of a stereogenic-at-Mo monopyrrolide-monoaryloxide.
J Am Chem Soc., 8 February 2012

Z-Selective Metathesis for Macrocycles
Tungsten catalysts dictate stereochemistry of double bond
C&EN, 7 November 2011

Catalytic Z-selective olefin cross-metathesis for natural product synthesis
Here we report catalytic Z-selective cross-metathesis reactions of terminal enol ethers.
Nature, 24 March 2011

Rigging Cross-Metathesis
Organic Synthesis: Molybdenum catalyst generates less stable Z olefin.
C&EN, 28 March 2011

Olefin Metathesis Highlights

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