Three component coupling reactions of N-acetyl-2-azetine- rapid stereoselective entry to 2,3,4-trisubstituted tetrahydroquinolines.
Three component coupling reactions of N-acetyl-2-azetine- rapid stereoselective entry to 2,3,4-trisubstituted tetrahydroquinolines.
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DOI：
10.1039/b110242g
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发表时间：
2002-02
影响因子：
4.9
通讯作者：
P. Stevenson;M. Nieuwenhuyzen;Daire Osborne
中科院分区：
文献类型：
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作者：
P. Stevenson;M. Nieuwenhuyzen;Daire Osborne
N-乙酰基-2-氮杂喹啉与芳胺衍生的亚胺进行刘易斯酸催化的[4 + 2]-环加成反应，得到外-内非对映异构的氮杂环丁烷环加成物的1：1混合物，其进一步与芳胺反应，以良好至优异的产率得到2，3，4-三取代的四氢喹啉，主要为一种非对映异构体。
N-Acetyl-2-azetine undergoes Lewis acid catalysed [4 + 2]-cycloaddition with imines derived from aromatic amines and gave a 1:1 mixture of exo-endo diastereoisomeric azetidine cycloadducts which reacted further with aromatic amine, to give 2,3,4-trisubsitituted tetrahydroquinolines in good to excellent yield, predominantly as one diastereoisomer.