Endo-selective enyne ring-closing metathesis promoted by stereogenic-at-Mo monoalkoxide and monoaryloxide complexes. Efficient synthesis of cyclic dienes not accessible through reactions with Ru carbenes
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Title
- Endo-selective enyne ring-closing metathesis promoted by stereogenic-at-Mo monoalkoxide and monoaryloxide complexes. Efficient synthesis of cyclic dienes not accessible through reactions with Ru carbenes
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Author(s)
- Lee, Y.-J.; Schrock, R.R.; Hoveyda, A.H.
- KIOST Author(s)
- Lee, Yeon Ju(이연주)
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Alternative Author(s)
- 이연주
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Publication Year
- 2009-08
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Abstract
- Stereogenic-at-Mo monoalkoxide and monoaryloxide complexes promote enyne ring-closing metathesis (RCM) reactions, affording the corresponding endo products with high selectivity (typically >98: <2 endo:exo). All catalysts can be prepared and used in situ. Five-, six-, and seven-membered rings are obtained through reactions with enyne substrates that bear all-carbon tethers as well as those that contain heteroatom substituents. The newly developed catalytic protocols complement the related exo-selective Ru-catalyzed processes. In cases where Ru-based complexes deliver exo and endo products nondiscriminately, such as when tetrasubstituted cyclic alkenes are generated, Mo-catalyzed reactions afford the endo product exclusively. The efficiency of synthesis of N- and O-containing endo diene heterocycles can be improved significantly through structural modification of Mo catalysts. The modularity of Mo-based monopyrrolides is thus exploited in the identification of the most effective catalyst variants. Through alteration of O-based monodentate ligands, catalysts have been identified that promote enyne RCM with improved efficiency. The structural attributes of three Mo complexes are elucidated through X-ray crystallography. The first examples of catalytic enantioselective enyne RCM reactions are reported (up to 98:2 enantiomer ratio and >98% endo). © 2009 American Chemical Society.
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ISSN
- 0002-7863
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URI
- https://sciwatch.kiost.ac.kr/handle/2020.kiost/4270
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DOI
- 10.1021/ja904098h
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Bibliographic Citation
- Journal of the American Chemical Society, v.131, no.30, pp.10652 - 10661, 2009
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Publisher
- American Chemical Society
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Type
- Article
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Language
- English
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Document Type
- Article
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