Construction of Complex Cyclobutane Building Blocks by Photosensitized [2 + 2] Cycloaddition of Vinyl Boronate Esters

Construction of Complex Cyclobutane Building Blocks by Photosensitized [2 + 2] Cycloaddition of Vinyl Boronate Esters

Cyclobutyl moieties in drug molecules are rare, and in general, they are minimally substituted and stereochemically simple. Methods to assemble structurally complex cyclobutane building blocks suitable for rapid diversification are thus highly desirable. We report herein a photosensitized [2 + 2] cy...

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Bibliographic Details
Published in:Organic letters Vol. 23; no. 9; pp. 3496 - 3501
Main Authors: Scholz, Spencer O, Kidd, Jesse B, Capaldo, Luca, Flikweert, Niecia E, Littlefield, Rowan M, Yoon, Tehshik P
Format: Journal Article
Language:English
Published: United States American Chemical Society 07-05-2021
Subjects:
Alkenes - chemistry
Boronic Acids - chemistry
Cycloaddition Reaction
Cyclobutanes - chemistry
Esters
Molecular Structure
Photosensitizing Agents
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Summary:Cyclobutyl moieties in drug molecules are rare, and in general, they are minimally substituted and stereochemically simple. Methods to assemble structurally complex cyclobutane building blocks suitable for rapid diversification are thus highly desirable. We report herein a photosensitized [2 + 2] cycloaddition with vinyl boronate esters affording straightforward access to complex, densely functionalized cyclobutane scaffolds. Mechanistic studies suggest an activation mode involving energy transfer to the styrenyl alkene rather than the vinyl boronate ester.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00938