Substituent effects in hydroxyiodination of 1,2-diacyloxycyclohex-3-enes

Sweeney, J.B., Knight, J.R. and Thobhani, S. (2006) Substituent effects in hydroxyiodination of 1,2-diacyloxycyclohex-3-enes. Tetrahedron, 62 (50). pp. 11565-11571. ISSN 0040-4020 doi: 10.1016/j.tet.2006.08.076

Abstract/Summary

The reaction of 1,2-diacyloxycyclohex-3-enes with iodinating agents in the presence of water has been investigated. The process is inherently diastereoselective, with many reactions giving only two of the four possible diastereoisomers which could be obtained. However, the regiocontrol is variable: highest selectivities are observed when pivalates are present on the periphery of the cycloalkene, when single regio- and diastereoisomers are obtained from the reactions. (c) 2006 Elsevier Ltd. All rights reserved.