Ring closing metathesis using chiral template consisting of hard and soft parts

Abstract

Macrocyclic compounds having 18-, 19-, 22-, and 23-membered rings were prepared quantitatively by ring closing metathesis of diene substrates consisting of a rigid o-or m-phthalate group and flexible but geometrically regulated 2, 4-pentanediol tethers. From the p-phthalate analogues, the ring closing metathesis and the cyclic dimmer formation were observed to give 24-membered ring (70% yield) and 40-membered ring (65% yield) respectively. Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.