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Issue 14, 2018
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Using stereoretention for the synthesis of E-macrocycles with ruthenium-based olefin metathesis catalysts

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Abstract

The synthesis of E-macrocycles is achieved using stereoretentive, Ru-based olefin metathesis catalysts supported by dithiolate ligands. Kinetic studies elucidate marked differences in activity among the catalysts tested, with catalyst 4 providing meaningful yields of products in much shorter reaction times than stereoretentive catalysts 2 and 3. Macrocycles were generated with excellent selectivity (>99% E) and in moderate to high yields (47–80% yield) from diene starting materials bearing two E-configured olefins. A variety of rings were constructed, ranging from 12- to 18-membered macrocycles, including the antibiotic recifeiolide.

Graphical abstract: Using stereoretention for the synthesis of E-macrocycles with ruthenium-based olefin metathesis catalysts

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Publication details

The article was received on 27 Jan 2018, accepted on 27 Feb 2018 and first published on 14 Mar 2018


Article type: Edge Article
DOI: 10.1039/C8SC00435H
Citation: Chem. Sci., 2018,9, 3580-3583
  • Open access: Creative Commons BY-NC license
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    Using stereoretention for the synthesis of E-macrocycles with ruthenium-based olefin metathesis catalysts

    T. S. Ahmed, T. P. Montgomery and R. H. Grubbs, Chem. Sci., 2018, 9, 3580
    DOI: 10.1039/C8SC00435H

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