Steric buttressing in the Pauson-Khand reactions of aryl enynes |
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Authors: | Christian E Madu |
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Institution: | Department of Chemistry and Biochemistry, The University of Texas at Arlington, Arlington, TX 76019-0065, United States |
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Abstract: | A variety of aryl enynes have been constructed from o-iodophenol derivatives containing ortho-tert-butyl groups via O-alkylation and a Sonogashira cross-coupling reaction. These substrates undergo efficient thermal and oxidative intramolecular Pauson-Khand reactions leading to the formation of sterically congested cyclopentenones, as well as the formation of medium-sized rings, although in the latter case with unusual regioselectivity. Incorporation of a TMS moiety on the alkyne group in a higher homolog led to cyclization via the normal mode, albeit in relatively low yield. |
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