Synthesis of Spirocyclic Enones by Rhodium‐Catalyzed Dearomatizing Oxidative Annulation of 2‐Alkenylphenols with Alkynes and Enynes | Zendy

Kujawa Szymon | Zendy; Best Daniel | Zendy; Burns David J. | Zendy; Lam Hon Wai | Zendy

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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.

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