American Chemical Society
ol0c02519_si_001.pdf (6.83 MB)

Chiral Naphthyl-C2-Indole as Scaffold for Phosphine Organocatalysis: Application in Asymmetric Formal [4 + 2] Cycloaddition Reactions

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journal contribution
posted on 2020-08-26, 22:05 authored by Tingting He, Lei Peng, Shan Li, Fangli Hu, Chuandong Xie, Shengli Huang, Shiqi Jia, Wenling Qin, Hailong Yan
The applications of a newly designed chiral naphthyl-C2-indole bifunctional phosphine organocatalyst in stereoselective formal [4 + 2] cycloaddition reactions were reported. The chiral naphthyl-C2-indole skeleton was introduced to bifunctional phosphine organocatalysis for the first time, and excellent stereocontrol was achieved in two types of formal [4 + 2] cycloaddition reactions. With the optimal catalyst, a series of chiral spirooxindole and hydrodibenzofuran architectures were produced in moderate to good yields with excellent stereoselectivities (up to >99% ee, >20:1 dr).