Stereoselective Access to Trisubstituted Cyclopentanols from Chiral Unsaturated Oxo Esters by Ketyl Radical Cyclization

S Feuillastre, B Pelotier, O Piva

Index: Feuillastre, Sophie; Pelotier, Beatrice; Piva, Olivier European Journal of Organic Chemistry, 2014 , vol. 2014, # 8 p. 1753 - 1759

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Abstract

Abstract Substituted cyclopentanols with three contiguous stereocenters were prepared with impressive diastereocontrol through a samarium diiodide induced 5-exo-trig radical process. The chiral unsaturated oxo ester precursors were prepared with ee values up to 90% from propionaldehyde through a two-step organocatalyzed aldolization and Wittig–Horner olefination reaction sequence.