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Facile Preparation of Spirolactones by an Alkoxycarbonyl Radical Cyclization–Cross‐Coupling Cascade
Author(s) -
Weires Nicholas A.,
Slutskyy Yuriy,
Overman Larry E.
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201903353
Subject(s) - electrophile , cascade , chemistry , aryl , oxalate , alcohol , combinatorial chemistry , coupling reaction , coupling (piping) , organic chemistry , medicinal chemistry , materials science , catalysis , metallurgy , alkyl , chromatography
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.