Faculty Publications

Title

Nucleophile-Selective Iodocyclizations: Butyrolactone versus Tetrahydrofuran Formation

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.

Original Publication Date

1-1-1989

DOI of published version

10.1021/ja00192a032

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