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Creators/Authors contains: "Holt, Eric"

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  1. ; ; ; ; ; ; ; ; (, The Journal of Organic Chemistry)
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  2. ; ; ; ; ; ; ; ; ; ; et al (, The Journal of Organic Chemistry)
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  3. ; ; ; ; ; (, Journal of Fluorine Chemistry)
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  4. ; ; ; ; ; ; ; ; ; ; et al (, The Journal of Organic Chemistry)
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  5. ; ; ; ; ; ; ; ; ; (, The Journal of Organic Chemistry)
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  6. ; ; ; ; ; ; (, Chemical Science)
    We report a photochemically induced, hydroxy-directed fluorination that addresses the prevailing challenge of high diastereoselectivity in this burgeoning field. Numerous simple and complex motifs showcase a spectrum of regio- and stereochemical outcomes based on the configuration of the hydroxy group. Notable examples include a long-sought switch in the selectivity of the refractory sclareolide core, an override of benzylic fluorination, and a rare case of 3,3′-difluorination. Furthermore, calculations illuminate a low barrier transition state for fluorination, supporting our notion that alcohols are engaged in coordinated reagent direction. A hydrogen bonding interaction between the innate hydroxy directing group and fluorine is also highlighted for several substrates with 19 F– 1 H HOESY experiments, calculations, and more. 
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