SUBSTITUENT-DIRECTED OXIDATION: REGIOCHEMISTRY AND STEREOCHEMISTRY OF THE ADDITION OF HYPERVALENT IODINE REAGENTS TO CYCLOALKENOLS.

Article abstract of DOI:10.1016/S0040-4039(00)96694-2

The transannular oxidative cyclization of 1-methylcyclooct-4-en-1-ol and cyclooct-4-en-1-ol was studied using hypervalent iodine reagents.The regioselectivity for the <3.3.1> vs. <4.2.1> 9-oxabicyclononane skeletons is low, but the additions is highly trans-selective; the results are rationalized in terms of a tricyclic oxonium ion intermediate.