Simple approach to modular chiral scaffolds: binding functional sulfur nucleophiles to Cinchona alkaloids

A series of functional modules were regio- and stereoselectively attached to the Cinchona alkaloid scaffolds. The S(N)2 reactions of thiolates with alkaloid mesylate and epoxide introduced metal-complexing moieties, including the heterocyclic systems of pyridine and 1,10-phenanthroline. The respective H-bond donating thiourea and salane motifs were formed in an additional step. The modified Cinchona alkaloids were tested in the metal-catalyzed Henry and Tsuji-Trost reactions. (C) 2015 Elsevier Ltd. All rights reserved.