Facile Preparation of Spirolactones by an Alkoxycarbonyl Radical Cyclization–Cross‐Coupling Cascade

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 h...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-06, Vol.58 (25), p.8561-8565
Main Authors: Weires, Nicholas A., Slutskyy, Yuriy, Overman, Larry E.
Format: Article
Language:English
Subjects:
Alcohols
Aromatic compounds
Coupling
cross-coupling
Drug discovery
dual-catalysis
Organic chemistry
Oxalic acid
photoredox
radical cyclization
spirolactones
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Summary: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. 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.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201903353