A Gold‐Catalyzed Domino Cyclization Enabling Rapid Construction of Diverse Polyheterocyclic Frameworks. Issue 1 (7th December 2017)

• Record Type: Journal Article
• Authors: He, Yi; Li, Zhenghua; Robeyns, Koen; Van Meervelt, Luc; Van der Eycken, Erik V.
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 1(2018)
• Page Start: 272
• Page End: 276
• Publication Date: 2017-12-07
• Subjects: dearomatization -- domino cyclization -- gold catalysis -- heterocycles -- Ugi reaction; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201710592
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: We report herein an efficient gold(I)‐catalyzed post‐Ugi domino dearomatization/ ipso ‐cyclization/Michael sequence that enables access to libraries of diverse (hetero)arene‐annulated tricyclic heterocycles. This process affords novel complex polycyclic scaffolds in moderate to good yields from readily available acyclic precursors with excellent chemo‐, regio‐, and diastereoselectivity. The power of this strategy has been demonstrated by the rapid synthesis of 40 highly functionalized polyheterocycles bearing indole, pyrrole, (benzo)furan, (benzo)thiophene, pyrazole, and electron‐rich arene groups in two operational steps. Abstract : Two‐stride synthesis : A post‐Ugi gold(I)‐catalyzed domino dearomatization/ ipso ‐cyclization/Michael sequence enabled facile access to diverse (hetero)arene‐annulated tricyclic heterocycles from readily available precursors. The power of this strategy was demonstrated by the rapid synthesis of 40 highly functionalized polyheterocycles containing indole, pyrrole, (benzo)furan, (benzo)thiophene, pyrazole, and electron‐rich arene groups.