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Visible-Light-Mediated Achmatowicz Rearrangement

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Plutschack,  Matthew B.
Kerry Gilmore, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Seeberger,  Peter H.
Peter H. Seeberger, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Gilmore,  Kerry
Kerry Gilmore, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society;

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Citation

Plutschack, M. B., Seeberger, P. H., & Gilmore, K. (2017). Visible-Light-Mediated Achmatowicz Rearrangement. Organic Letters, 19(1), 30-33. doi:10.1021/acs.orglett.6b03237.


Cite as: http://hdl.handle.net/11858/00-001M-0000-002C-2824-7
Abstract
Visible-light-mediated photoredox catalysis is a viable method to access highly reactive intermediates from cheap, readily available, and shelf-stable reagents to perform clean chemical transformations. Here, we report the first photoredox-catalyzed Achmatowicz reaction of furfuryl alcohol derivatives to produce functionalized dihydropyranones while only forming easily separable NaHSO4 as a byproduct. The water solubility of the byproduct facilitates direct Boc-protection of the resulting hemiacetal without the need for column purification. The reaction is very robust and permits the use of various aqueous solutions and light sources including sunlight.