Water Overcomes Methyl Group Directing Effects in Epoxide-Opening Cascades
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Jamison_Water overcomes.pdf
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Author(s)
Morten, Christopher J.
Jamison, Timothy F.
Date Issued
April 2009
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Morten, Christopher J., and Timothy F. Jamison. “Water Overcomes Methyl Group Directing Effects in Epoxide-Opening Cascades.” Journal of the American Chemical Society 131, no. 19 (May 20, 2009): 6678-6679.
Version
Author's final manuscript
Abstract
Water is an effective promoter of the endo-selective opening of trisubstituted epoxides, enabling related cascades leading to a variety of substituted ladder polyether structures. When used in conjunction with a tetrahydropyran-templated nucleophile, water can overcome the powerful electronic directing effect of a methyl substituent at either site of the epoxide, making water a uniquely versatile medium and promoter of epoxide opening.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
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DOI of Published Version
https://doi.org/10.1021/ja9025243
