Synthesis of Linear (Z)-α,β-Unsaturated Esters by Catalytic Cross-Metathesis. The Influence of Acetonitrile
Author(s)
Yu, Elsie C.; Johnson, Brett M.; Hoveyda, Amir H.; Townsend, Erik M.; Schrock, Richard Royce
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Kinetically controlled catalytic cross-metathesis reactions that generate (Z)-α,β-unsaturated esters selectively are disclosed. A key finding is that the presence of acetonitrile obviates the need for using excess amounts of a more valuable terminal alkene substrates. On the basis of X-ray structure and spectroscopic investigations a rationale for the positive impact of acetonitrile is provided. Transformations leading to various E,Z-dienoates are highly Z-selective as well. Utility is highlighted by application to stereoselective synthesis of the C1–C12 fragment of biologically active natural product (−)-laulimalide.
Date issued
2016-10Department
Massachusetts Institute of Technology. Department of ChemistryJournal
Angewandte Chemie International Edition
Publisher
Wiley-Blackwell
Citation
Yu, Elsie C., et al. “Synthesis of Linear ( Z )-α,β-Unsaturated Esters by Catalytic Cross-Metathesis. The Influence of Acetonitrile.” Angewandte Chemie International Edition, vol. 55, no. 42, Oct. 2016, pp. 13210–14.
Version: Author's final manuscript
ISSN
1433-7851