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个人信息Personal Information
教授
硕士生导师
性别：男
毕业院校：大连理工大学
学位：硕士
所在单位：化工学院
学科：有机化学. 应用化学
电子邮箱：chenhb@dlut.edu.cn
Organocatalytic [3+2] cycloaddition of oxindole-based azomethine ylides with 3-nitrochromenes: a facile approach to enantioenriched polycyclic spirooxindole-chromane adducts
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论文类型：期刊论文
发表时间：2018-02-07
发表刊物：ORGANIC & BIOMOLECULAR CHEMISTRY
收录刊物：SCIE、EI、PubMed
卷号：16
期号：5
页面范围：807-815
ISSN号：1477-0520
摘要：An organocatalytic asymmetric [3 + 2] cycloaddition of oxindole-based azomethine ylides with 3-nitro-2H-chromenes has been developed. This reaction provides a facile approach to densely functionalized polycyclic spirooxindole-chromane adducts featuring four contiguous stereogenic centers, including two tetrasubstituted carbon centers. The products were obtained in high yields with good to excellent stereoselectivities (up to 99% yields, 96% ee and >20 : 1 dr). In addition, the spiro[pyrrolidine-2,3'-oxindole]chromane adducts could be readily derivatized via simple oxidation and reduction treatment. A dual activation working model to illuminate the stereochemical course of the [3 + 2] cycloaddition event is proposed.