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  Visible-light-mediated Achmatowicz rearrangement

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.

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Item Permalink: http://hdl.handle.net/11858/00-001M-0000-002C-2824-7 Version Permalink: http://hdl.handle.net/21.11116/0000-0006-597A-E
Genre: Journal Article

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 Creators:
Plutschack, Matthew B.1, Author              
Seeberger, Peter H.2, Author              
Gilmore, Kerry1, Author              
Affiliations:
1Kerry Gilmore, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863304              
2Peter H. Seeberger - Automated Systems, Biomolekulare Systeme, Max Planck Institute of Colloids and Interfaces, Max Planck Society, ou_1863306              

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Free keywords: Open Access
 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.

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 Dates: 2016-12-122017
 Publication Status: Published in print
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 Identifiers: DOI: 10.1021/acs.orglett.6b03237
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Title: Organic Letters
  Other : Org. Lett.
Source Genre: Journal
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Publ. Info: Washington, DC : American Chemical Society
Pages: - Volume / Issue: 19 (1) Sequence Number: - Start / End Page: 30 - 33 Identifier: ISSN: 1523-7060