Highly stereoselective syntheses of all 1,2,3-Me,OH,Me triads via asymmetric hydrogenation reactions

Abstract

Iridium-catalyzed asymmetric hydrogenations of chiral alkenes were used to access four pivotal α,ω-functionalized chirons, that contain widely occurring stereochemical 1,2,3-Me,OH,Me motifs. A chiral analogue of Crabtree's catalyst was used in key hydrogenation steps to form these motifs with high stereochemical purities. An application of one of these chirons is illustrated here with a synthesis of (-)-invictolide. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.