A Traceless Tether Strategy for Achieving Formal Intermolecular Hexadehydro-Diels-Alder Reactions

Merrick Pierson Smela; Thomas R. Hoye

doi:10.1021/acs.orglett.8b02473

A Traceless Tether Strategy for Achieving Formal Intermolecular Hexadehydro-Diels-Alder Reactions

Merrick Pierson Smela, Thomas R. Hoye

Chemistry (Twin Cities)

Research output: Contribution to journal › Article › peer-review

12 Scopus citations

Abstract

A synthetic strategy formally equivalent to an intermolecular hexadehydro-Diels-Alder (HDDA) reaction is described. Sulfur-based linkers were designed and constructed by joining terminal alkynes or diynes using alkyne thiolate chemistry. The resulting tetraynes and triynes successfully underwent HDDA cyclization and benzyne trapping. Linker removal by reductive desulfurization was uneventful. The strategy was also found suitable for the tetradehydro-Diels-Alder (TDDA) reaction.

Original language	English (US)
Pages (from-to)	5502-5505
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	17
DOIs	https://doi.org/10.1021/acs.orglett.8b02473
State	Published - Sep 7 2018

Bibliographical note

Funding Information:
Support for this work was provided by the Institute of General Medical Sciences of the U.S. Department of Health and Human Services (R01 GM65597, then R35 GM127097). M.P.S. was supported by a Gleysteen−Heisig summer fellowship and by the University of Minnesota Undergraduate Research Opportunities Program.

Publisher Copyright:
© 2018 American Chemical Society.

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https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6354248

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abstract = "A synthetic strategy formally equivalent to an intermolecular hexadehydro-Diels-Alder (HDDA) reaction is described. Sulfur-based linkers were designed and constructed by joining terminal alkynes or diynes using alkyne thiolate chemistry. The resulting tetraynes and triynes successfully underwent HDDA cyclization and benzyne trapping. Linker removal by reductive desulfurization was uneventful. The strategy was also found suitable for the tetradehydro-Diels-Alder (TDDA) reaction.",

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A Traceless Tether Strategy for Achieving Formal Intermolecular Hexadehydro-Diels-Alder Reactions

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