Nucleophile-Selective Iodocyclizations: Butyrolactone Versus Tetrahydrofuran Formation

Authors

Mark J. Kurth, University of California, Davis
Richard L. Beard, University of California, Davis
Marilyn Olmstead, University of California, Davis
James G. Macmillan, University of Northern IowaFollow

Document Type

Article

Journal/Book/Conference Title

Journal of the American Chemical Society

Volume

111

Issue

10

First Page

3712

Last Page

3717

Abstract

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.

Department

Department of Chemistry

Original Publication Date

1-1-1989

DOI of published version

10.1021/ja00192a032

Recommended Citation

Kurth, Mark J.; Beard, Richard L.; Olmstead, Marilyn; and Macmillan, James G., "Nucleophile-Selective Iodocyclizations: Butyrolactone Versus Tetrahydrofuran Formation" (1989). Faculty Publications. 4660.
https://scholarworks.uni.edu/facpub/4660