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

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• 作者：Mariola Zielińska-Błajet ; Przemysław J. Boratyński ; Łukasz Sidorowicz ; Jacek Skarżewski ; ^{jacek.skarzewski@pwr.wroc.pl" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Cinchona alkaloids ; Sulfur nucleophiles ; Epoxide ring opening ; Carbon&ndash ; sulfur bond formation
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：26 May 2016
• 年：2016
• 卷：72
• 期：21
• 页码：2643-2648
• 全文大小：456 K

文摘

A series of functional modules were regio- and stereoselectively attached to the Cinchona alkaloid scaffolds. The S_N2 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.