Synthesis of Linear (Z)-α,β-Unsaturated Esters by Catalytic Cross-Metathesis. The Influence of Acetonitrile
Name
nihms-835896.pdf
Size
876.87 KB
Format
Adobe PDF
Checksum (MD5)
6a62dfa8dae6a42b34238fb7ed8148de
Author(s)
Yu, Elsie C.
Johnson, Brett M.
Hoveyda, Amir H.
Townsend, Erik M.
Schrock, Richard Royce
Date Issued
October 2016
Journal
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
Abstract
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Creative Commons Attribution-Noncommercial-Share Alike
Persistent DSpace Link
DOI of Published Version
https://doi.org/10.1002/ANIE.201608087
