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.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2803343 | PMC |
| http://dx.doi.org/10.1021/ja9025243 | DOI Listing |
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