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Alkynes to (Free) Carbenes to Polycyclic Cyclopropanes

https://doi.org/10.1021/jacs.4c10897

Guzman, Alexander L; Mann, Alexis N; Hoye, Thomas R (October 2024, Journal of the American Chemical Society)

ABSTRACT: Carbenes and carbenoids are commonly employed for the synthesis of cyclopropane-containing compounds. Here we report the metal-free, intramolecular cyclopropanation of tethered alkenes by free carbenes derived from alkynes to construct structurally unique, multicyclic cyclopropanes with perfect atom economy. The nature of the tether influences both the rate of carbene formation as well as subsequent competing reaction events. Some of the substrates lead to metastable cyclopropane intermediates that further fragment to furnish interesting isomeric products by mechanistically novel processes. A removable siloxane tether can be utilized to achieve formal intermolecular cyclopropanations and to access cyclopropanol derivatives.
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2:1 Adducts Arising from Reactions between Benzynes and 1,3,4-Oxadiazoles

https://doi.org/10.1021/acs.orglett.4c01005

Guzman, Alexander L.; Kevorkian, Paul V.; Hoye, Thomas R. (April 2024, Organic Letters)

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TMS is Superior to Residual CHCl3 for Use as the Internal Reference for Routine 1H NMR Spectra Recorded in CDCl3

https://doi.org/10.1021/acs.joc.1c02590

Guzman, Alexander L.; Hoye, Thomas R. (January 2022, Journal of organic chemistry)

Editor's Choice Featured Article https://pubs.acs.org/doi/full/10.1021/acs.joc.1c02590
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