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Gold‐Catalyzed endo ‐Cyclizations of 1,4‐Diynes to Seven‐Membered Ring Heterocycles
Author(s) -
Wilckens Kristina,
Uhlemann Marcus,
Czekelius Constantin
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901702
Subject(s) - cycloisomerization , ring (chemistry) , scheme (mathematics) , catalysis , chemistry , combinatorial chemistry , stereochemistry , computer science , information retrieval , organic chemistry , mathematics , mathematical analysis
endo ‐Rule for gold : A highly endo ‐selective gold‐catalyzed cycloisomerization of 1,4‐diynes was developed. By employing electron‐rich phosphines and N‐heterocyclic carbenes as ligands, a number of 1,4‐diynes could be cyclized in a desymmetrizing fashion to form dihydrodioxepines and enantiomerically enriched tetrahydrooxazepines (see scheme).