Gold-Catalyzed Post-Ugi Ipso-Cyclization with Switchable Diastereoselectivity

A gold-catalyzed post-Ugi ipso-cyclization for the diastereoselective synthesis of spirocyclic pyrrol-2-one-dienone system is described. Tuning the catalytic system, solvent, and temperature allowed selectively attaining two sets of diastereoisomers. The scope of the process has been evaluated, and a putative mechanistic model was proposed. © 2018 American Chemical Society.

Authors
Nechaev A.A. 1 , Van Hecke K. , Zaman M. 3 , Kashtanov S. 4 , Ungur L. 5 , Pereshivko O.P. 3 , Peshkov V.A. 3 , Van Der Eycken E.V.
Journal
Journal of Organic Chemistry
Issue number
15
Language
English
Pages
8170-8182
State
Published
Link
External link
DOI
10.1021/ACS.JOC.8B00953
Volume
83
Year
2018
Organizations
  • 1 Laboratory of Organic and Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, Leuven, B-3001, Belgium
  • 2 X Struct, Department of Chemistry, Ghent University, Krijgslaan 281-S3, Ghent, B-9000, Belgium
  • 3 College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Dushu Lake Campus, Suzhou, 215123, China
  • 4 Institute of Functional Nano and Soft Materials (FUNSOM), Jiangsu Key Laboratory for Carbon-Based Functional Materials and Devices, Soochow University, Suzhou, 215123, China
  • 5 Theory of Nanomaterials Group, Department of Chemistry, University of Leuven (KU Leuven), Celestijnenlaan 200F, Leuven, B-3001, Belgium
  • 6 Peoples' Friendship University of Russia, RUDN University, Miklukho-Maklaya Street 6, Moscow, 117198, Russian Federation
Keywords
Catalysis; Gold; Stereoselectivity; Catalytic system; Diastereo-selectivity; Diastereoisomers; Diastereoselective synthesis; Mechanistic modeling; Switchable; Cyclization
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