Enantioselective thiourea-catalyzed acyl-Mannich reactions of isoquinolines

Abstract

(Chemical Equation Presented) Inexpensive aromatic feedstocks are substrates for highly enantioselective acylative Mannich reactions catalyzed by a thiourea chiral hydrogen-bond donor 1. This methodology provides access to useful 1-substituted dihydroisoquinolines (see scheme; TrocCl = 2,2,2-trichloroethyl chloroformate, TBS = tert-butyldimethylsilyl), which serve as precursors to enantioenriched 1-substituted tetrahydroisoquinolines. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.