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Nickel-catalyzed formation of cyclopentenone derivatives via the unique cycloaddition of α,β-unsaturated phenyl esters with alkynes.
J Am Chem Soc. 2011 Sep 28; 133(38):14900-3.JA

Abstract

Oxygen-containing organic compounds, such as ethers, carboxylates, and carbamates, have recently received increasing attention because of their newly discovered applications as electrophiles in cross-coupling reactions via transition metal-catalyzed C-O bond activation. However, no cycloaddition reaction involving their C-O bond activation has been demonstrated thus far. The present study developed a Ni(0)-catalyzed unique [3+2] cycloaddition reaction of α,β-unsaturated phenyl esters with alkynes in (i)PrOH to yield cyclopentenone derivatives.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Ohashi M
Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka, Japan. ohashi@chem.eng.osaka-u.ac.jp
Taniguchi T
No affiliation info available
Ogoshi S
No affiliation info available

MeSH

AlkynesCatalysisCyclizationCyclopentanesEstersMolecular StructureNickelOrganometallic CompoundsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

21877707

Citation

Ohashi, Masato, et al. "Nickel-catalyzed Formation of Cyclopentenone Derivatives Via the Unique Cycloaddition of Α,β-unsaturated Phenyl Esters With Alkynes." Journal of the American Chemical Society, vol. 133, no. 38, 2011, pp. 14900-3.
Ohashi M, Taniguchi T, Ogoshi S. Nickel-catalyzed formation of cyclopentenone derivatives via the unique cycloaddition of α,β-unsaturated phenyl esters with alkynes. J Am Chem Soc. 2011;133(38):14900-3.
Ohashi, M., Taniguchi, T., & Ogoshi, S. (2011). Nickel-catalyzed formation of cyclopentenone derivatives via the unique cycloaddition of α,β-unsaturated phenyl esters with alkynes. Journal of the American Chemical Society, 133(38), 14900-3. https://doi.org/10.1021/ja2059999
Ohashi M, Taniguchi T, Ogoshi S. Nickel-catalyzed Formation of Cyclopentenone Derivatives Via the Unique Cycloaddition of Α,β-unsaturated Phenyl Esters With Alkynes. J Am Chem Soc. 2011 Sep 28;133(38):14900-3. PubMed PMID: 21877707.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Nickel-catalyzed formation of cyclopentenone derivatives via the unique cycloaddition of α,β-unsaturated phenyl esters with alkynes. AU - Ohashi,Masato, AU - Taniguchi,Tomoaki, AU - Ogoshi,Sensuke, Y1 - 2011/08/30/ PY - 2011/9/1/entrez PY - 2011/9/1/pubmed PY - 2012/1/6/medline SP - 14900 EP - 3 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 133 IS - 38 N2 - Oxygen-containing organic compounds, such as ethers, carboxylates, and carbamates, have recently received increasing attention because of their newly discovered applications as electrophiles in cross-coupling reactions via transition metal-catalyzed C-O bond activation. However, no cycloaddition reaction involving their C-O bond activation has been demonstrated thus far. The present study developed a Ni(0)-catalyzed unique [3+2] cycloaddition reaction of α,β-unsaturated phenyl esters with alkynes in (i)PrOH to yield cyclopentenone derivatives. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/21877707/Nickel_catalyzed_formation_of_cyclopentenone_derivatives_via_the_unique_cycloaddition_of_αβ_unsaturated_phenyl_esters_with_alkynes_ L2 - https://doi.org/10.1021/ja2059999 DB - PRIME DP - Unbound Medicine ER -