Nucleophile-Selective Iodocyclizations: Butyrolactone versus Tetrahydrofuran Formation
Journal of the American Chemical Society
Nucleophile selectivity in the electrophilic cyclization of substrates like 3 has been investigated in the context of efficient chemo- and stereoselective functionalization of3-hydroxy-2-(2-methylenecyclohexan-1-yl)butyric acids (cf., 6–9) via iodocyclization.In addition, composite nucleophile selectivities for this diastereomeric series were used toprobe 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. © 1989, American Chemical Society. All rights reserved.
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DOI of published version
Kurth, Mark J.; Beard, Richard L.; Olmstead, Marilyn; and Macmillan, James G., "Nucleophile-Selective Iodocyclizations: Butyrolactone versus Tetrahydrofuran Formation" (1989). Faculty Publications. 4660.