Water Overcomes Methyl Group Directing Effects in Epoxide-Opening Cascades
Author(s)Morten, Christopher J.; Jamison, Timothy F.
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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.
DepartmentMassachusetts Institute of Technology. Department of Chemistry
Journal of the American Chemical Society
American Chemical Society (ACS)
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.
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