New synthetic strategies for the stereocontrolled synthesis of substituted ‘skipped’ diepoxides
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Jamison_New synthetic strategies.pdf
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1.56 MB
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Author(s)
Morten, Christopher J.
Jamison, Timothy F.
Date Issued
June 2009
Journal
Tetrahedron
Publisher
Elsevier
Citation
Morten, Christopher J., and Timothy F. Jamison. “New Synthetic Strategies for the Stereocontrolled Synthesis of Substituted ‘skipped’ Diepoxides.” Tetrahedron 65, no. 33 (August 2009): 6648–6655.
Version
Author's final manuscript
Abstract
This report describes a number of new synthetic approaches toward methyl-substituted mono- and diepoxy alcohols that serve as substrates for endo-selective epoxide-opening cascades. The key transformations involve the manipulation of alkynes. Highlighted are the directed methylmetalation of bishomopropargylic alcohols, the bromoallylation of alkynes, and Pd-catalyzed cross-coupling between an alkenyl boronate ester and allylic bromides.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Creative Commons Attribution-Noncommercial-NoDerivatives
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DOI of Published Version
https://doi.org/10.1016/j.tet.2009.05.074
