Tags

Type your tag names separated by a space and hit enter

Palladium-catalyzed reactions of cyclohexadienones: regioselective cyclizations triggered by alkyne acetoxylation.
Org Lett. 2009 Sep 03; 11(17):3998-4000.OL

Abstract

Regioselective cyclizations of alkyne-tethered cyclohexadienones can be accomplished under palladium catalysis. The cyclization involves an initial Pd-mediated acetoxylation of the alkyne, followed by migratory insertion and protonolysis of the resulting palladium enolate. The predictable regioselectivity of these atom-economical and stereoselective reactions is influenced by developing steric interactions during migratory insertion of a vinyl palladium intermediate.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Tello-Aburto R
Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
Harned AM
No affiliation info available

MeSH

AlkynesCatalysisCyclizationCyclohexenesModels, MolecularMolecular StructurePalladiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

19708708

Citation

Tello-Aburto, Rodolfo, and Andrew M. Harned. "Palladium-catalyzed Reactions of Cyclohexadienones: Regioselective Cyclizations Triggered By Alkyne Acetoxylation." Organic Letters, vol. 11, no. 17, 2009, pp. 3998-4000.
Tello-Aburto R, Harned AM. Palladium-catalyzed reactions of cyclohexadienones: regioselective cyclizations triggered by alkyne acetoxylation. Org Lett. 2009;11(17):3998-4000.
Tello-Aburto, R., & Harned, A. M. (2009). Palladium-catalyzed reactions of cyclohexadienones: regioselective cyclizations triggered by alkyne acetoxylation. Organic Letters, 11(17), 3998-4000. https://doi.org/10.1021/ol901642w
Tello-Aburto R, Harned AM. Palladium-catalyzed Reactions of Cyclohexadienones: Regioselective Cyclizations Triggered By Alkyne Acetoxylation. Org Lett. 2009 Sep 3;11(17):3998-4000. PubMed PMID: 19708708.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-catalyzed reactions of cyclohexadienones: regioselective cyclizations triggered by alkyne acetoxylation. AU - Tello-Aburto,Rodolfo, AU - Harned,Andrew M, PY - 2009/8/28/entrez PY - 2009/8/28/pubmed PY - 2009/9/24/medline SP - 3998 EP - 4000 JF - Organic letters JO - Org Lett VL - 11 IS - 17 N2 - Regioselective cyclizations of alkyne-tethered cyclohexadienones can be accomplished under palladium catalysis. The cyclization involves an initial Pd-mediated acetoxylation of the alkyne, followed by migratory insertion and protonolysis of the resulting palladium enolate. The predictable regioselectivity of these atom-economical and stereoselective reactions is influenced by developing steric interactions during migratory insertion of a vinyl palladium intermediate. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/19708708/Palladium_catalyzed_reactions_of_cyclohexadienones:_regioselective_cyclizations_triggered_by_alkyne_acetoxylation_ L2 - https://doi.org/10.1021/ol901642w DB - PRIME DP - Unbound Medicine ER -