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Synthesis of spirocyclic enones by rhodium-catalyzed dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes.
Chemistry. 2014 Jul 07; 20(28):8599-602.C

Abstract

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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Publisher Full Text (DOI)

Authors+Show Affiliations

Kujawa S
EaStCHEM, School of Chemistry, University of Edinburgh, Joseph Black Building, The King's Buildings, West Mains Road, Edinburgh, EH9 3 JJ (UK) and School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD (UK).
Best D
No affiliation info available
Burns DJ
No affiliation info available
Lam HW
No affiliation info available

MeSH

AlkynesCatalysisCyclizationMolecular StructureOxidation-ReductionRhodium

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

24909937

Citation

Kujawa, Szymon, et al. "Synthesis of Spirocyclic Enones By Rhodium-catalyzed Dearomatizing Oxidative Annulation of 2-alkenylphenols With Alkynes and Enynes." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 20, no. 28, 2014, pp. 8599-602.
Kujawa S, Best D, Burns DJ, et al. Synthesis of spirocyclic enones by rhodium-catalyzed dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes. Chemistry. 2014;20(28):8599-602.
Kujawa, S., Best, D., Burns, D. J., & Lam, H. W. (2014). Synthesis of spirocyclic enones by rhodium-catalyzed dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes. Chemistry (Weinheim an Der Bergstrasse, Germany), 20(28), 8599-602. https://doi.org/10.1002/chem.201403454
Kujawa S, et al. Synthesis of Spirocyclic Enones By Rhodium-catalyzed Dearomatizing Oxidative Annulation of 2-alkenylphenols With Alkynes and Enynes. Chemistry. 2014 Jul 7;20(28):8599-602. PubMed PMID: 24909937.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of spirocyclic enones by rhodium-catalyzed dearomatizing oxidative annulation of 2-alkenylphenols with alkynes and enynes. AU - Kujawa,Szymon, AU - Best,Daniel, AU - Burns,David J, AU - Lam,Hon Wai, Y1 - 2014/06/06/ PY - 2014/05/08/received PY - 2014/6/10/entrez PY - 2014/6/10/pubmed PY - 2015/5/15/medline KW - CH activation KW - alkyne KW - enyne KW - phenol KW - rhodium SP - 8599 EP - 602 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 20 IS - 28 N2 - 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. SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/24909937/Synthesis_of_spirocyclic_enones_by_rhodium_catalyzed_dearomatizing_oxidative_annulation_of_2_alkenylphenols_with_alkynes_and_enynes_ DB - PRIME DP - Unbound Medicine ER -