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Asymmetric α-Allylation of Amino Acid Esters with Alkynes Enabled by Chiral Aldehyde/Palladium Combined Catalysis
Organic Letters ( IF 4.9 ) Pub Date : 2024-09-10 , DOI: 10.1021/acs.orglett.4c02840 Yao Lin 1 , Wei Wen 1 , Jian-Hua Liu 1 , Fang Zhu 1 , Chao-Xing Li 1 , Zhu-Lian Wu 1 , Tian Cai 1 , Chen-Jiang Liu 2 , Qi-Xiang Guo 1
Organic Letters ( IF 4.9 ) Pub Date : 2024-09-10 , DOI: 10.1021/acs.orglett.4c02840 Yao Lin 1 , Wei Wen 1 , Jian-Hua Liu 1 , Fang Zhu 1 , Chao-Xing Li 1 , Zhu-Lian Wu 1 , Tian Cai 1 , Chen-Jiang Liu 2 , Qi-Xiang Guo 1
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A highly efficient, atom-economical α-allylation reaction of NH2-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.
中文翻译：
手性醛/钯联合催化下氨基酸酯与炔烃的不对称α-烯丙基化
通过手性醛/钯联合催化，实现了NH 2 -未保护的氨基酸酯和炔烃的高效、原子经济的α-烯丙基化反应。生产多种 α,α-二取代非蛋白原 α-氨基酸酯，产率 31-92%，ee 值 84-97%。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。
更新日期：2024-09-10
中文翻译：
手性醛/钯联合催化下氨基酸酯与炔烃的不对称α-烯丙基化
通过手性醛/钯联合催化，实现了NH 2 -未保护的氨基酸酯和炔烃的高效、原子经济的α-烯丙基化反应。生产多种 α,α-二取代非蛋白原 α-氨基酸酯，产率 31-92%，ee 值 84-97%。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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