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 SCIE SCOPUS

Cited 68 time in WEB OF SCIENCE Cited 81 time in Scopus
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
Author(s)
Lee, Y.-J.; Schrock, R.R.; Hoveyda, A.H.
KIOST Author(s)
Lee, Yeon Ju(이연주)
Publication Year
2009-08
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.
ISSN
0002-7863
URI
https://sciwatch.kiost.ac.kr/handle/2020.kiost/4270
DOI
10.1021/ja904098h
Bibliographic Citation
Journal of the American Chemical Society, v.131, no.30, pp.10652 - 10661, 2009
Publisher
American Chemical Society
Type
Article
Language
English
Document Type
Article
Publisher
American Chemical Society
Related Researcher
Research Interests

Marine Natural Product,Natural Product Biosynthesis,Medicinal Chemistry,해양 천연물,천연물 생합성,의약화학

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