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

Authors :
Nechaev, Anton A.
Van Hecke, Kristof
Zaman, Manzoor
Kashtanov, Stepan
Ungur, Liviu
Pereshivko, Olga P.
Peshkov, Vsevolod A.
Van der Eycken, Erik V.
Source :
The Journal of Organic Chemistry; July 2018, Vol. 83 Issue: 15 p8170-8182, 13p
Publication Year :
2018

Abstract

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.

Details

Language :
English
ISSN :
00223263
Volume :
83
Issue :
15
Database :
Supplemental Index
Journal :
The Journal of Organic Chemistry
Publication Type :
Periodical
Accession number :
ejs45946250
Full Text :
https://doi.org/10.1021/acs.joc.8b00953