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

F Beaumier, M Dupuis, C Spino…

Index: Beaumier, Francis; Dupuis, Marianne; Spino, Claude; Legault, Claude Y. Journal of the American Chemical Society, 2012 , vol. 134, # 13 p. 5938 - 5953

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Citation Number: 12

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 ...