Bimetallic Gold(I)/Chiral N,N′-Dioxide Nickel(II) Asymmetric Relay Catalysis: Chemo- and Enantioselective Synthesis of Spiroketals and Spiroaminals

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• 作者：Jun Li ; Dr. Lili Lin ; Bowen Hu ; Xiangjin Lian ; Gang Wang ; Prof. Dr. Xiaohua Liu and Prof. Dr. Xiaoming Feng
• 刊名：Angewandte Chemie
• 出版年：2016
• 出版时间：May 10, 2016
• 年：2016
• 卷：128
• 期：20
• 页码：6179-6182
• 全文大小：709K
• ISSN：1521-3757

文摘

A highly efficient asymmetric cascade reaction between keto esters and alkynyl alcohols and amides is reported. The success of the reaction was attributed to the combination of chiral Lewis acid N,N′-dioxide nickel(II) catalysis with achiral π-acid gold(I) catalysis working as an asymmetric relay catalytic system. The corresponding spiroketals and spiroaminals were synthesized in up to 99 % yield, 19:1 d.r., and more than 99 % ee under mild reaction conditions. Control experiments suggest that the N,N′-dioxide ligand was essential for the formation of the spiro products.