Journal of the American Chemical Society · 1989 · 23 citations · 0 references
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.