Selective Synthesis of E-Macrocycles

  • Author: ChemistryViews.org
  • Published: 29 March 2018
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Chemical Science/Royal Society of Chemistry
  • Associated Societies: Royal Society of Chemistry (RSC), UK
thumbnail image: Selective Synthesis of <i>E</i>-Macrocycles

Transition-metal-catalyzed ring-closing metathesis is a useful tool for organic synthesis. The stereochemistry of the resulting olefin is important for the properties of the product, and the E- and Z- isomers can be difficult to separate. Thus, finding stereoselective approaches to ring-closing metathesis is important.


Robert H. Grubbs, California Institute of Technology (Caltech), Pasadena, USA, and colleagues have developed a ruthenium-based metathesis catalyst for the stereoretentive synthesis of E-macrocycles (pictured). The team prepared ruthenium complexes bearing N-heterocyclic carbene (NHC) and dithiolate ligands. Thes catalysts were then used to convert diene starting materials bearing two E-olefins into the corresponding 12- to 18-membered E-macrocycles.


The reactions proceed in moderate to good yields and with high selectivities (up to 99 % E). According to the researchers, the selectivity is due to a sterically favored arrangement in the metallacyclobutane intermediate.


 

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