Asymmetric Michael Addition of Aldimino Esters with Chalcones Catalyzed by Silver/Xing-Phos: Mechanism-Oriented Divergent Synthesis of Chiral Pyrrolines
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- 作者：Xing-Feng Bai ; Dr. Li Li ; Dr. Zheng Xu ; Dr. Zhan-Jiang Zheng ; Prof. Dr. Chun-Gu Xia ; Dr. Yu-Ming Cui and Prof. Dr. Li-Wen Xu
- 刊名：Chemistry - A European Journal
- 出版年：2016
- 出版时间：July 18, 2016
- 年：2016
- 卷：22
- 期：30
- 页码：10399-10404
- 全文大小：544K
- ISSN：1521-3765
文摘
The mechanism-oriented reaction design for the divergent synthesis of chiral molecules from simple starting materials is highly desirable. In this work, aromatic amide-derived nonbiarylatropisomer/silver (silver/Xing-Phos) complex was used to catalyze the Michael addition of glycine aldimino esters to chalcones and successfully applied to the subsequent cyclocondensation to afford substituted cis-Δ(1)-pyrroline derivatives with up to 98 % ee. Besides the inherent performance of the chiral Ag/Xing-Phos catalyst system, it was found that the workup of such reactions played an important role for the stereoselective construction of stereodivergent Δ(1)-pyrrolines, in which an epimerization of the cis-Δ(1)-pyrrolines to the trans-isomers during was revealed.