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

Merrick Pierson Smela, Thomas R. Hoye

Research output: Contribution to journalArticlepeer-review

5 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 languageEnglish (US)
Pages (from-to)5502-5505
Number of pages4
JournalOrganic Letters
Volume20
Issue number17
DOIs
StatePublished - 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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