Affiliation:
1. Université Paris-Saclay CNRS ICMMO 91400 Orsay France
Abstract
AbstractA 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.
Reference67 articles.
1.
2. E. V. Anslyn D. A. Dougherty inModern Physical Organic Chemistry; University Science Books: Sausalito CA 2006 pp 65–145;
3. Z. Rappoport J. F. Liebman inThe Chemistry of Cyclobutanes; Wiley: Chichester UK 2005;
4.