Magnesium-Induced Cyclizations of 2-(3-Iodopropyl)cycloalkanones. A Cyclopentane Annelation Method

Article abstract of DOI:10.1021/jo00148a024

A process for the stereoselective construction of a cyclopentane ring onto a preexisting cycloalkanone is developed. 2-(3-Iodopropyl)cycloalkanones, obtained by known methods from the parent cyclic ketones, were converted to bicycloalkan-1-ols in moderate to good yields by magnesium in THF.This cyclization shows a large preference for formation of the cis compounds.Attempts to extend this reaction to the formation of six- and seven-membered rings were largely unsuccessful.