ol6b00710_si_002.cif (22.06 kB)

Highly Chemo- and Regioselective Construction of Spirocarbocycles by a Pd(0)-Catalyzed Dearomatization of Phenol-Based Biaryls with 1,3-Dienes

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posted on 2016-04-27, 13:53 authored by Lei Luo, Huayu Zheng, Jingjing Liu, Hui Wang, Yaoyu Wang, Xinjun Luan
A novel Pd(0)-catalyzed intermolecular carbocyclization of phenol-derived biaryls with 1,3-dienes has been implemented through a sequence of oxidative addition to the C–I bond, regioselective olefin insertion, and allylative dearomatization. This method provides a broad range of attractive spirocyclic compounds bearing two contiguous tertiary/quaternary carbon centers in good yields with excellent chemoselectivity and regioselectivity. Moreover, preliminary results indicate that asymmetric control of this process is feasible with chiral ligands.