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Rhenium-catalyzed formation of bicyclo[3.3.1]nonene frameworks by a reaction of cyclic beta-keto esters with terminal alkynes.
Org Lett. 2009 Jun 18; 11(12):2535-7.OL

Abstract

Treatment of cyclic beta-keto esters with terminal alkynes in the presence of a catalytic amount of a rhenium complex, [ReBr(CO)(3)(thf)](2), gave bicyclo[3.3.1]nonene derivatives. The reaction conditions and yields of the bicyclo[3.3.1]nonenes were improved by the sequential use of tetrabutylammonium fluoride (TBAF) after the rhenium-catalyzed reactions.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Kuninobu Y
Division of Chemistry and Biochemistry, Graduate School of Natural Science and Technology, Okayama University, Tsushima, Kita-ku, Okayama 700-8530, Japan. kuninobu@cc.okayama-u.ac.jp
Morita J
No affiliation info available
Nishi M
No affiliation info available
Kawata A
No affiliation info available
Takai K
No affiliation info available

MeSH

AlkynesBridged Bicyclo CompoundsCatalysisCrystallography, X-RayCyclizationEstersMolecular StructureQuaternary Ammonium CompoundsRhenium

Pub Type(s)

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

Language

eng

PubMed ID

19456121

Citation

Kuninobu, Yoichiro, et al. "Rhenium-catalyzed Formation of Bicyclo[3.3.1]nonene Frameworks By a Reaction of Cyclic Beta-keto Esters With Terminal Alkynes." Organic Letters, vol. 11, no. 12, 2009, pp. 2535-7.
Kuninobu Y, Morita J, Nishi M, et al. Rhenium-catalyzed formation of bicyclo[3.3.1]nonene frameworks by a reaction of cyclic beta-keto esters with terminal alkynes. Org Lett. 2009;11(12):2535-7.
Kuninobu, Y., Morita, J., Nishi, M., Kawata, A., & Takai, K. (2009). Rhenium-catalyzed formation of bicyclo[3.3.1]nonene frameworks by a reaction of cyclic beta-keto esters with terminal alkynes. Organic Letters, 11(12), 2535-7. https://doi.org/10.1021/ol900772h
Kuninobu Y, et al. Rhenium-catalyzed Formation of Bicyclo[3.3.1]nonene Frameworks By a Reaction of Cyclic Beta-keto Esters With Terminal Alkynes. Org Lett. 2009 Jun 18;11(12):2535-7. PubMed PMID: 19456121.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhenium-catalyzed formation of bicyclo[3.3.1]nonene frameworks by a reaction of cyclic beta-keto esters with terminal alkynes. AU - Kuninobu,Yoichiro, AU - Morita,Junya, AU - Nishi,Mitsumi, AU - Kawata,Atsushi, AU - Takai,Kazuhiko, PY - 2009/5/22/entrez PY - 2009/5/22/pubmed PY - 2009/10/7/medline SP - 2535 EP - 7 JF - Organic letters JO - Org Lett VL - 11 IS - 12 N2 - Treatment of cyclic beta-keto esters with terminal alkynes in the presence of a catalytic amount of a rhenium complex, [ReBr(CO)(3)(thf)](2), gave bicyclo[3.3.1]nonene derivatives. The reaction conditions and yields of the bicyclo[3.3.1]nonenes were improved by the sequential use of tetrabutylammonium fluoride (TBAF) after the rhenium-catalyzed reactions. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/19456121/Rhenium_catalyzed_formation_of_bicyclo[3_3_1]nonene_frameworks_by_a_reaction_of_cyclic_beta_keto_esters_with_terminal_alkynes_ L2 - https://doi.org/10.1021/ol900772h DB - PRIME DP - Unbound Medicine ER -