An access to highly enantioenriched cis -3,5-disubstituted γ-lactones from α-bromoacetate and silyl enol ether

A novel synthetic strategy for highly enantioenriched -3,5-disubstituted γ-lactones has been developed by the AgOTf-promoted nucleophilic substitution of α-bromoacetates with silyl enol ethers and subsequent reductive lactonization. The utility of this synthetic method was further demonstrated throu...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2021-09, Vol.19 (35), p.7655-7663
Main Authors: Lee, Ha Rim, Kim, Seo Yun, Park, Min Ji, Park, Yong Sun
Format: Article
Language:English
Subjects:
Ethers
Lactones
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Summary:A novel synthetic strategy for highly enantioenriched -3,5-disubstituted γ-lactones has been developed by the AgOTf-promoted nucleophilic substitution of α-bromoacetates with silyl enol ethers and subsequent reductive lactonization. The utility of this synthetic method was further demonstrated through the concise stereodivergent synthesis of - and -2,4-disubstituted tetrahydrofurans.
ISSN:1477-0520
1477-0539
DOI:10.1039/d1ob01403j