Asymmetric [3+2] Annulations of Thioaurone and Aurone Derivatives for the Construction of Spiroheterocycles. Issue 4 (18th March 2021)

• Record Type: Journal Article
• Authors: Liu, Bao‐Xin; Yan, Ru‐Jie; Li, Xiao‐Xun; Du, Wei; Chen, Ying‐Chun
• Is Part Of: Asian journal of organic chemistry. Volume 10:Issue 4(2021)
• Page Start: 784
• Page End: 787
• Publication Date: 2021-03-18
• Subjects: spiroheterocycles -- (thio)aurone -- Morita–Baylis–Hillman carbonates -- [3+2] annulation -- allylic ylides; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202100078
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: Aurones and their analogues are convenient two‐atom units for the rapid construction of valuable spiroheterocycles. Here, we demonstrate that the Morita–Baylis–Hillman carbonates of isatins can be efficiently assembled with thioaurones, aurones, or even methyleneindolinones in a highly asymmetric [3+2] annulation manner, affording a broad spectrum of densely functionalized spiro‐benzothiophene, ‐benzofuran and bisspirooxindole frameworks in high yields with good to excellent stereoselectivity. Abstract : Thioaurones and aurones can be chemo‐ and regioselectively assembled with Morita–Baylis–Hillman carbonates of isatins in a [3+2] annulation manner under the catalysis of a chiral DMAP‐type Lewis base, furnishing densely functionalized spiro‐benzothiophene and ‐benzofuran frameworks in high yields with good to excellent enantioselectivity.