Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 140, Issue 20, Pages 6212-6216Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b03063
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Funding
- NCI [R01 CA126827]
- American Cancer Society [09-016-01 CDD]
- NIGMS [T32GM105538]
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An enantioselective cross-dehydrogenative coupling (CDC) reaction to access tetrahydropyrans has been developed. This process combines in situ Lewis acid activation of a nucleophile in concert with the oxidative formation of a transient oxocarbenium electrophile, leading to a productive and highly enantioselective CDC. These advances represent one of the first successful applications of CDC for the enantioselective couplings of unfunctionalized ethers. This system provides efficient access to valuable tetrahydropyran motifs found in many natural products and bioactive small molecules.
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