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- Title
A Highly Efficient Synthesis of Z-Macrocycles Using Stereoretentive, Ruthenium-Based Metathesis Catalysts.
- Authors
Ahmed, Tonia S.; Grubbs, Robert H.
- Abstract
A highly efficient, Z-selective ring-closing metathesis system for the formation of macrocycles using a stereoretentive, ruthenium-based catalyst supported by a dithiolate ligand is reported. The catalyst is remarkably active as observed in initiation experiments showing complete catalyst initiation at −20 °C within 10 minutes. Macrocyclization reactions generated Z-products from easily accessible diene starting materials bearing a Z-olefin moiety. This approach provides a more efficient and selective route to Z-macrocycles relative to previously reported systems. Reactions were completed within shorter reaction times, and turnover numbers of up to 100 could be achieved. Macrocyclic lactones ranging in size from twelve- to seventeen-membered rings were synthesized in moderate to high yields (67-79 %) with excellent Z-selectivity (95-99 %).
- Subjects
MACROCYCLIC compound synthesis; RUTHENIUM catalysts; LIGANDS (Chemistry); METATHESIS reactions; TURNOVER frequency (Catalysis); RING formation (Chemistry)
- Publication
Angewandte Chemie, 2017, Vol 129, Issue 37, p11365
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201704670