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 language | English (US) |
|---|---|
| Pages (from-to) | 3712-3717 |
| Number of pages | 6 |
| Journal | Journal of the American Chemical Society |
| Volume | 111 |
| Issue number | 10 |
| State | Published - 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.