手性醛/钯联合催化实现氨基酸酯与炔烃的不对称α-烯丙基化反应
Asymmetric α-Allylation of Amino Acid Esters with Alkynes Enabled by Chiral Aldehyde/Palladium Combined Catalysis.
作者信息
Lin Yao, Wen Wei, Liu Jian-Hua, Zhu Fang, Li Chao-Xing, Wu Zhu-Lian, Cai Tian, Liu Chen-Jiang, Guo Qi-Xiang
机构信息
Key Laboratory of Applied Chemistry of Chongqing Municipality, and Chongqing Key Laboratory of Soft-Matter Material Chemistry and Function Manufacturing, School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, China.
Urumqi Key Laboratory of Green Catalysis and Synthesis Technology, Key Laboratory of Oil and Gas Fine Chemicals, Ministry of Education & Xinjiang Uygur Autonomous Region, State Key Laboratory of Chemistry and Utilization of Carbon Based Energy Resources, College of Chemistry, Xinjiang University, Urumqi 830017, China.
出版信息
Org Lett. 2024 Sep 20;26(37):7908-7913. doi: 10.1021/acs.orglett.4c02840. Epub 2024 Sep 10.
A highly efficient, atom-economical α-allylation reaction of NH-unprotected amino acid esters and alkynes is achieved by chiral aldehyde/palladium combined catalysis. A diverse range of α,α-disubstituted nonproteinogenic α-amino acid esters are produced in 31-92% yields and 84-97% ee values. The allylation products are utilized for the synthesis of drug molecule BMS561392 and other chiral molecules possessing complex structures. Mechanistic investigations reveal that this reaction proceeds via a chiral aldehyde-/palladium-mediated triple cascade catalytic cycle.
通过手性醛/钯联合催化实现了未保护氨基的氨基酸酯与炔烃的高效、原子经济的α-烯丙基化反应。以31% - 92%的产率和84% - 97%的对映体过量值制备了多种α,α-二取代的非蛋白质ogenicα-氨基酸酯。烯丙基化产物用于合成药物分子BMS561392和其他具有复杂结构的手性分子。机理研究表明，该反应通过手性醛/钯介导的三重级联催化循环进行。
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