Asymmetric Synthesis of Dihydrocoumarins Containing Contiguous Quaternary and Tertiary Stereogenic Centers Catalyzed by a Cinchona ‐Alkaloid‐Based Bifunctional Thiourea Derivative

作者：Shao‐Yun Zhang, Ming Lv, Shao‐Jie Yin, Nai‐Kai Li, Jun‐Qi Zhang, Xing‐Wang Wang · 发表于：Advanced Synthesis & Catalysis · 年份：2016 · DOI：10.1002/adsc.201500666 · 被引用次数：38 · 研究领域：Synthesis of Indole Derivatives、Synthesis and Biological Activity、Asymmetric Synthesis and Catalysis

Abstract A series of enantiomerically enriched 3,4‐dihydrocoumarins containing contiguous quaternary and tertiary stereogenic centers has been efficiently constructed via domino asymmetric Michael addition/transesterification reactions of azlactones with o ‐hydroxychalcones using a quinine‐derived thiourea as bifunctional organocatalyst. Under mild reaction conditions, the optically active 3,4‐dihydrocoumarins were generally obtained in 63–96% yields with >20:1 dr and 81–96% ee . magnified image