Construction of polycyclic spirooxindoles through [3+2] annulations of Morita–Baylis–Hillman carbona

• 作 者: Kai-Kai Wang Wei Du Jin Zhu Ying-Chun Chen
• 机 构: Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences,University of Chinese Academy of
• 出 处: Chinese Chemical Letters
• 发表日期: 2017年03期
• 关键词: polycyclic Baylis nitro fused chiral catalyzed DMAP carbonate quaternary indole

A mild and efficient dearomatic [3+2] annulation reaction of 3-nitro-7-azaindoles and Morita Baylis Hillman carbonates from isatins was developed catalyzed by DMAP, affording the corresponding polycyclic spirooxindoles containing fused azaindoline architectures and vicinal quaternary centers in excellent yields(up to 96%) with high regio- and diastereoselectivity(dr > 19:1). Moderate enantioselectivity(79% ee) was obtained by employing a chiral DMAP-type Lewis base catalyst.

A mild and efficient dearomatic [3 + 2] annulation reaction of 3-nitro-7-azaindoles and Morita Baylis Hillman carbonates from isatins was developed catalyzed by DMAP, affording the corresponding polycyclic spirooxindoles containing fused azaindoline architectures and vicinal quaternary centers in excellent yields ( up to 96%) with high regio- and diastereoselectivity (dr> 19: 1). Moderate enantioselectivity (79% ee) was obtained by employing a chiral DMAP-type Lewis base catalyst.