Build/Couple/Pair Strategy Combining the Petasis 3-Component Reaction with Ru-Catalyzed Ring-Closing Metathesis and Isomerization

Erhad Ascic, Sebastian Thordal Le Quement, Mette Ishøy, Mathilde Daugaard, Thomas Eiland Nielsen

Research output: Contribution to journalJournal articleResearchpeer-review

Abstract

A “build/couple/pair” pathway for the systematic synthesis of structurally diverse small molecules is presented. The Petasis 3-component reaction was used to synthesize anti-amino alcohols displaying pairwise reactive combinations of alkene moieties. Upon treatment with a ruthenium alkylidene-catalyst, these dienes selectively underwent ring-closing metathesis reactions to form 5- and 7-membered heterocycles and cyclic aminals via a tandem isomerization/N-alkyliminium cyclization sequence.
Original languageEnglish
JournalA C S Combinatorial Science
Volume14
Issue number4
Pages (from-to)253-257
ISSN2156-8952
DOIs
Publication statusPublished - 2012

Keywords

  • Petasis 3-component reaction
  • ring-closing metathesis
  • isomerization
  • build/couple/pair

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