- Terminal olefins to chromans, isochromans, and pyrans via allylic C-H oxidation
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The synthesis of chroman, isochroman, and pyran motifs has been accomplished via a combination of Pd(II)/bis-sulfoxide C-H activation and Lewis acid co-catalysis. A wide range of alcohols are found to be competent nucleophiles for the transformation under uniform conditions (catalyst, solvent, temperature). Mechanistic studies suggest that the reaction proceeds via initial C-H activation followed by a novel inner-sphere functionalization pathway. Consistent with this, the reaction shows reactivity trends orthogonal to those of traditional Pd(0)-catalyzed allylic substitutions.
- Ammann, Stephen E.,Rice, Grant T.,White, M. Christina
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supporting information
p. 10834 - 10837
(2014/08/18)
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- THE SYNTHESIS OF HOMOTWISTANES BY THE TANDEM WESSELY OXIDATION - DIELS-ALDER REACTION SEQUENCE
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Wessely oxidation of 5-(2-hydroxyphenyl)-1-pentene and -1-penten-3-ones followed by intramolecular Diels-Alder reactions gave homotwistanes; similar treatment of 5-(2-hydroxyphenyl)-3-methylene-1-pentene gave twistane and isotwistane derivatives.
- Bhamare, N. K.,Granger, Thierry,John, C. R.,Yates, Peter
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p. 4439 - 4442
(2007/10/02)
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