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Synthesis of Heterocycles through a Ruthenium‐Catalyzed Tandem Ring‐Closing Metathesis/Isomerization/N‐Acyliminium Cyclization Sequence
Author(s) -
Ascic Erhad,
Jensen Jakob F.,
Nielsen Thomas E.
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201100417
Subject(s) - iminium , ring closing metathesis , metathesis , chemistry , isomerization , ruthenium , nucleophile , tandem , combinatorial chemistry , heteroatom , total synthesis , intramolecular force , stereochemistry , salt metathesis reaction , ring (chemistry) , catalysis , organic chemistry , polymer , materials science , composite material , polymerization
Tandem bicycle : In the title reaction double bonds created during ring‐closing metathesis isomerize to generate reactive iminium intermediates that undergo intramolecular cyclization reactions with tethered heteroatom and carbon nucleophiles. In this way, a series of biologically interesting heterocyclic compounds can be made, including a known precursor for the total synthesis of the antiparasitic natural product harmicine.