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Synthesis of Spirocyclic Enones by Rhodium‐Catalyzed Dearomatizing Oxidative Annulation of 2‐Alkenylphenols with Alkynes and Enynes
Author(s) -
Kujawa Szymon,
Best Daniel,
Burns David J.,
Lam Hon Wai
Publication year - 2014
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.201403454
Subject(s) - annulation , catalysis , chemistry , rhodium , oxidative phosphorylation , ring (chemistry) , stoichiometry , combinatorial chemistry , medicinal chemistry , organic chemistry , biochemistry
The dearomatizing oxidative annulation of 2‐alkenylphenols with alkynes and enynes proceeds with high yields and regioselectivities under Rh III catalysis. These reactions are successful using Cu(OAc) 2 or air as the stoichiometric oxidant, and provide spirocyclic enones, the basic ring system of which appears in several natural products. Application of this process to the preparation of a highly functionalized tetracycle is also demonstrated.