喹啉-2- 1的化学和对映选择性分子间烯丙基化

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-12-08 DOI:10.1002/adsc.202401113

Zihao Li, Yumeng Wang, Yuqiao Zhou, Zongli Xiong, Jian Wang, Weijun Yao, Zhen Wang

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引用次数: 0

摘要

研究了喹啉-2(1H)- 1分子间C-、O-和N-烯丙基对映选择性反应。在pd催化下，3-羟基喹诺酮与boc保护的MBH加合物反应生成一系列1,4-二氢喹啉-2,3-二酮，产率为20-95%，对映选择性为69-96%。此外，通过改变苯甲醛的有机催化剂和boc保护的MBH加合物，可以发生邻丙烯基烷基化。此外，3- o保护喹啉-2- 1与烯丙酸酯也实现了n-烯丙基化（产率40-92%，ee 78-97%）。

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Chemo- and Enantioselective Intermolecular Allylation of Quinolin-2-ones

An enantioselective C-, O- and N- intermolecular allylic reaction of quinolin-2(1H)-ones has been developed. The reaction between 3-hydroxy quinolone and Boc-protected MBH adducts with Pd-catalysis provided a series of 1,4-dihydroquinoline-2,3-diones in 20-95% yield accompanied by 69-96% enantioselectivity. In addition, the O-allylic alkylation could occur by varying the organo-catalyst and Boc-protected MBH adducts from benzaldehyde. Furthermore, the N-allylation of 3-O-protected quinolin-2-ones with allylic acetates was also realized (40-92% yield, 78-97% ee).

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来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.