American Chemical Society
jo502209f_si_004.cif (28.51 kB)

AlCl3‑Promoted Selective Michael Addition with Allenoate and Methyleneindolinone: Synthesis of Spirocyclic Oxindole by Using Allenoate as a Four-Carbon Component Building Block

Download (28.51 kB)
posted on 2014-11-21, 00:00 authored by Shibo Xu, Chunju Li, Xueshun Jia, Jian Li
The AlCl3-promoted cyclization of readily available allenoates with methyleneindolinone is disclosed. The present strategy provides a rapid access to spirocyclic oxindole-cyclohexenones in an efficient manner. Remarkably, the allenoate is implemented as a four-carbon (4C) component to form the ring, which shows high synthetic efficiency. Flexibility of this method allows quick synthesis of spirocyclic oxindole-dihydropyrans by varying one of the components. It is also noteworthy that AlCl3 serves as the chlorine source as well as an effective catalyst to facilitate this interesting transformation.