Functionalized Alkylidenecyclobutanes from a Cyclopent‐2‐enone Substrate via a Tandem Photochemical Transformation and an Allylic Substitution Protocol
Xiaodan Yu,
Thomas Boddaert,
David J. Aitken
Abstract:A four‐step metal‐free procedure is described for the transformation of 4‐hydroxy‐2‐methylcyclopent‐2‐enone derivatives into highly functionalized E‐alkylidenecyclobutanes featuring oxygenated tetrasubstituted centers. The key intermediate is a (cyclobutenyl)propane‐1,3‐diol diester, easily accessed via a tandem photochemical reaction, which undergoes an original Brønsted acid‐catalyzed allylic substitution reaction with alcohols to give the title products with ester‐protected primary alcohol side chains.
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