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      Formal intramolecular (4 + 1)-cycloaddition of dialkoxycarbenes: control of the stereoselectivity and a mechanistic portrait.

      Journal of the American Chemical Society

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          Abstract

          The stereoselective synthesis of 5-5, 6-5, and 7-5 fused O-heterocyclic compounds is reported. The key reaction is a formal intramolecular (4 + 1)-cycloaddition involving a dialkoxycarbene and an electron-deficient diene where the stereoselectivity is dependent on the length of the tether. An analysis of the stereochemical outcome of this reaction sheds light on its complex mechanistic picture. High-level calculations were used to support the proposed mechanistic portrait.

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          Journal
          22404454
          10.1021/ja211927b

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