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

Anton A. Nechaev, Kristof Van Hecke, Manzoor Zaman, Stepan Kashtanov, Liviu Ungur, Olga P. Pereshivko, Vsevolod A. Peshkov, Erik V. Van Der Eycken

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)8170-8182
Number of pages13
JournalJournal of Organic Chemistry
Volume83
Issue number15
DOIs
Publication statusPublished - Aug 3 2018
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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