Hydroxy-Assisted Regio- and Stereoselective Synthesis of Functionalized 4‑Methylenepyrrolidine Derivatives via Phosphine-Catalyzed [3 + 2] Cycloaddition of Allenoates with o‑Hydroxyaryl Azomethine Ylides
posted on 2017-11-03, 00:00authored byZhusheng 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.