Lewis Acid-catalyzed [3+2]Cycloaddition of Alkynes with N-Tosylaziridines via Carbon-Carbon Bond Cleavage: Synthesis of Highly Substituted 3-Pyrrolines

Lewis Acid-catalyzed [3+2]Cycloaddition of Alkynes with N-Tosylaziridines via Carbon-Carbon Bond Cleavage: Synthesis of Highly Substituted 3-Pyrrolines
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DOI:
10.1021/ol202603e
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发表时间:
2011-11-18
期刊:
影响因子:
5.2
通讯作者:
Zhang, Junliang
Zhang, Junliang
中科院分区:
化学1区
文献类型:
--
作者:
Li, Lei;Zhang, Junliang

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本文报道了一种新的、高效的、高选择性的刘易斯酸催化的炔与偶氮甲碱叶立德的[3 + 2]环加成反应。通过应用市售手性Pybox 7作为配体可以实现中等的对映选择性(70%ee)。
A novel, efficient, and highly regloselective Lewis acid-catalyzed [3 + 2] cycloaddition of alkynes with azomethine ylides, which are easily obtained from N-tosylaziridines via C-C bond heterolysis at room temperature was developed. Moderate enantioselectivity (70% ee) can be achieved by the application of the commercially available chiral Pybox 7 as the ligand.