A practical strategy for the structural diversification of aliphatic scaffolds through the palladium-catalyzed picolinamide-directed remote functionalization of unactivated C(sp3)-H bonds

Abstract

Hats off to the director: High levels of regio- and stereoselectivity were observed for a broad range of amine substrates with aryl and vinyl iodide coupling partners in the title reaction. The synthetic utility of this strategy was highlighted by the ready preparation from threonine of 1, with a removable picolinamide auxiliary PAr, and its coupling with 2 in a concise formal synthesis of (+)-obafluorin. TBS=tert-butyldimethylsilyl. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.