Pheromone Synthesis via Organoboranes: A Stereospecific Synthesis of (Z)-7-Alken-1-ols

Abstract

Treatment of trans-1-alkenylborepanes, obtained via monohydroboration of 1-alkynes with borepane, with iodine in the presence of a base results in the migration of one end of the cycloalkyl chain from boron to the adjacent carbon, producing intermediates containing the eight-membered borocane moiety, which undergoes a rapid deiodoboronation to afford the (Z)-7-alkenyl-1-boronate esters. These boronate esters on oxidation produce (Z)-7-alken-1-ols, providing a general, one-pot, and stereospecific synthesis of (Z)-7-alken-1-ols. © 1982, American Chemical Society. All rights reserved.