857270-96-3Relevant articles and documents
Formal intramolecular (4 + 1)-cycloaddition of dialkoxycarbenes: Control of the stereoselectivity and a mechanistic portrait
Beaumier, Francis,Dupuis, Marianne,Spino, Claude,Legault, Claude Y.
, p. 5938 - 5953 (2012/05/07)
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.