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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
StatePublished - 2012
Peer-reviewedYes
CitationsWeb of Science® Times Cited: 20

Keywords

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