Nucleophile-selective iodocyclizations: Butyrolactone versus tetrahydrofuran formation

Mark J. Kurth, Richard L. Beard, Marilyn Olmstead, James G. Macmillan

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Abstract

Nucleophile selectivity in the electrophilic cyclization of substrates like 3 has been investigated in the context of efficient chemo- and stereoselective functionalization of 3-hydroxy-2-(2-methylenecyclohexan-1-yl)butyric acids (cf., 6-9) via iodocyclization. In addition, composite nucleophile selectivities for this diastereomeric series were used to probe the reliability of ground-state conformational analysis as an indicator of relative reactivities for the various conformations of 3. The results provide unambiguous evidence for C1′,C2,C3 stereocontrol in these kinetic iodocyclizations.

Original languageEnglish (US)
Pages (from-to)3712-3717
Number of pages6
JournalJournal of the American Chemical Society
Volume111
Issue number10
StatePublished - 1989

ASJC Scopus subject areas

  • Chemistry(all)

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    Kurth, M. J., Beard, R. L., Olmstead, M., & Macmillan, J. G. (1989). Nucleophile-selective iodocyclizations: Butyrolactone versus tetrahydrofuran formation. Journal of the American Chemical Society, 111(10), 3712-3717.