American Chemical Society
jo7b02560_si_002.pdf (15.69 MB)

Hydroxy-Assisted Regio- and Stereoselective Synthesis of Functionalized 4‑Methylenepyrrolidine Derivatives via Phosphine-Catalyzed [3 + 2] Cycloaddition of Allenoates with o‑Hydroxyaryl Azomethine Ylides

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journal contribution
posted on 2017-11-03, 00:00 authored by Zhusheng Huang, Yishu Bao, Yu Zhang, Fulai Yang, Tao Lu, Qingfa Zhou
In this work, we present a new strategy for the chemo-, regio-, and stereoselective synthesis of functionalized pyrrolidine derivatives via a hydroxy-assisted phosphine-catalyzed reaction of allenoates or substituted allenoates with o-hydroxyaryl azomethine ylides that offers a wide variety of 4-methylenepyrrolidine derivatives in synthetically useful yields with high stereoselctivities under mild conditions. Remarkably, it is the first example of highly regio- and stereoselective phosphine-catalyzed [3 + 2] cycloaddition of allenoates with o-hydroxyaryl azomethine ylides.