Highly Z- and Enantioselective Ring-Opening/Cross-Metathesis Reactions Catalyzed by Stereogenic-at-Mo Adamantylimido Complexes
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Schrock_Highly z.pdf
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Author(s)
Ibrahem, Ismail
Yu, Miao
Hoveyda, Amir H.
Schrock, Richard Royce
Date Issued
February 2009
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Ibrahem, Ismail, Miao Yu, Richard R. Schrock, and Amir H. Hoveyda. “Highly Z- and Enantioselective Ring-Opening/Cross-Metathesis Reactions Catalyzed by Stereogenic-at-Mo Adamantylimido Complexes.” Journal of the American Chemical Society 131, no. 11 (March 25, 2009): 3844-3845.
Version
Author's final manuscript
Abstract
The first highly Z- and enantioselective class of ring-opening/cross-metathesis reactions is presented. Transformations are promoted in the presence of <2 mol % of chiral stereogenic-at-Mo monoaryloxide complexes bearing an adamantylimido ligand that are prepared and used in situ. Reactions involve meso oxabicyclic substrates and afford the desired pyrans in 50−85% yield and up to >98:<2 enantiomer ratio. Importantly, the desired chiral pyrans thus obtained bear a Z olefin either exclusively (>98:<2 Z/E) or predominantly (≥87:13 Z/E).
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/ja900097n
