Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 77, Issue 14, Pages 6332-6339Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo300939f
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Funding
- Boehringer Ingelheim (Canada) Ltd.
- Natural Sciences and Engineering Research Council of Canada
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In addition to their utility in Barton-McCombie deoxygenations, xanthates can engage in 5-exo-trig radical cyclizations to afford lactones after oxidative workup. In this paper, we describe a tin-free protocol that provides direct access to lactones via hydrolysis of labile thioketal intermediates. Analysis of several systems of varying complexity reveals that the reaction is most applicable for constrained systems in which the reacting center is prepositioned near the radical-accepting alkene.
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