Issue 14, 2018

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
27 Janv. 2018
Accepted
27 Febr. 2018
First published
14 Marts 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2018,9, 3580-3583

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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