Facile Preparation of Spirolactones by an Alkoxycarbonyl Radical Cyclization–Cross‐Coupling Cascade. Issue 25 (13th May 2019)

• Record Type: Journal Article
• Authors: Weires, Nicholas A.; Slutskyy, Yuriy; Overman, Larry E.
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 25(2019)
• Page Start: 8561
• Page End: 8565
• Publication Date: 2019-05-13
• Subjects: cross-coupling -- dual-catalysis -- photoredox -- radical cyclization -- spirolactones; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201903353
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: An alkoxycarbonyl radical cyclization–cross‐coupling cascade has been developed that allows functionalized γ‐butyrolactones to be prepared in one step from simple tertiary alcohol‐derived homoallylic oxalate precursors. The reaction succeeds with aryl and vinyl electrophiles and is compatible with heterocyclic fragments in both coupling partners. This chemistry allows for the rapid construction of spirolactones, which are of interest in drug discovery endeavors. Abstract : An alkoxycarbonyl radical 5‐exo cyclization–cross‐coupling cascade has been developed that allows functionalized γ‐butyrolactones to be prepared in one step from simple tertiary alcohol‐derived homoallylic oxalate precursors. The reaction succeeds with aryl and vinyl electrophiles and is compatible with heterocyclic fragments in both coupling partners. This chemistry allows for the rapid construction of spirolactones, which are of interest in drug discovery endeavors.