Asymmetric construction of pyrido[1, 2-a]-1H-indole derivatives via a gold-catalyzed cycloisomerization. Issue 2 (12th November 2020)

• Record Type: Journal Article
• Authors: Jiang, Feng; Fu, Chunling; Ma, Shengming
• Is Part Of: Chemical science. Volume 12:Issue 2(2021)
• Page Start: 696
• Page End: 701
• Publication Date: 2020-11-12
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/d0sc05619g
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : We reported an IPrAuCl/AgSbF6 -catalyzed cycloisomerization of enantio-enriched N -1, 3-disubstituted allenylindoles affording optically active pyrido[1, 2- a ]-1 H -indoles in excellent yields and enantioselectivities. Abstract : Pyrido[1, 2- a ]-1 H -indoles are important scaffolds found in many biologically active compounds. Herein, we first developed an IPrAuCl/AgSbF6 -catalyzed cycloisomerization of N -1, 3-disubstituted allenyl indoles affording pyrido[1, 2- a ]-1 H -indoles. Then the axial-to-central chirality transfer starting from enantio-enriched N -1, 3-disubstituted allenylindoles affording optically active pyrido[1, 2- a ]-1 H -indoles has been realized in excellent yields and enantioselectivities. A mechanism has been proposed based on mechanistic studies. Synthetic applications have also been demonstrated.