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A general and regioselective synthesis of cyclopentenone derivatives through nickel(0)-mediated [3 + 2] cyclization of alkenyl Fischer carbene complexes and internal alkynes.
J Am Chem Soc. 2007 Nov 21; 129(46):14422-6.JA

Abstract

A broad range of substituted 2-cyclopentenone derivatives 3-6 are synthesized by the nickel(0)-mediated [3 + 2] cyclization reaction of chromium alkenyl(methoxy)carbene complexes 1 and internal alkynes 2. The reaction takes place with complete regioselectivity with both unactivated alkynes and activated alkynes (electron-withdrawing and electron-donating substituted alkynes). Representative cycloadducts containing boron and tin substituents are further demonstrated to be active partners in classical Pd-catalyzed C-C coupling processes to allow the production of 2-aryl- and 2-alkynyl-substituted cyclopentenones 9-13.

Authors+Show Affiliations

Barluenga J
Instituto Universitario de Química Organometálica Enrique Moles, Unidad Asociada al CSIC, Universidad de Oviedo, Oviedo, Spain. barluenga@uniovi.es
Barrio P
No affiliation info available
Riesgo L
No affiliation info available
López LA
No affiliation info available
Tomás M
No affiliation info available

MeSH

AlkenesAlkynesBoronCatalysisCyclizationCyclopentanesHydrocarbonsMethaneModels, ChemicalNickelPalladiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

17967020

Citation

Barluenga, José, et al. "A General and Regioselective Synthesis of Cyclopentenone Derivatives Through Nickel(0)-mediated [3 + 2] Cyclization of Alkenyl Fischer Carbene Complexes and Internal Alkynes." Journal of the American Chemical Society, vol. 129, no. 46, 2007, pp. 14422-6.
Barluenga J, Barrio P, Riesgo L, et al. A general and regioselective synthesis of cyclopentenone derivatives through nickel(0)-mediated [3 + 2] cyclization of alkenyl Fischer carbene complexes and internal alkynes. J Am Chem Soc. 2007;129(46):14422-6.
Barluenga, J., Barrio, P., Riesgo, L., López, L. A., & Tomás, M. (2007). A general and regioselective synthesis of cyclopentenone derivatives through nickel(0)-mediated [3 + 2] cyclization of alkenyl Fischer carbene complexes and internal alkynes. Journal of the American Chemical Society, 129(46), 14422-6.
Barluenga J, et al. A General and Regioselective Synthesis of Cyclopentenone Derivatives Through Nickel(0)-mediated [3 + 2] Cyclization of Alkenyl Fischer Carbene Complexes and Internal Alkynes. J Am Chem Soc. 2007 Nov 21;129(46):14422-6. PubMed PMID: 17967020.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A general and regioselective synthesis of cyclopentenone derivatives through nickel(0)-mediated [3 + 2] cyclization of alkenyl Fischer carbene complexes and internal alkynes. AU - Barluenga,José, AU - Barrio,Pablo, AU - Riesgo,Lorena, AU - López,Luis A, AU - Tomás,Miguel, Y1 - 2007/10/30/ PY - 2007/10/31/pubmed PY - 2008/2/22/medline PY - 2007/10/31/entrez SP - 14422 EP - 6 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 129 IS - 46 N2 - A broad range of substituted 2-cyclopentenone derivatives 3-6 are synthesized by the nickel(0)-mediated [3 + 2] cyclization reaction of chromium alkenyl(methoxy)carbene complexes 1 and internal alkynes 2. The reaction takes place with complete regioselectivity with both unactivated alkynes and activated alkynes (electron-withdrawing and electron-donating substituted alkynes). Representative cycloadducts containing boron and tin substituents are further demonstrated to be active partners in classical Pd-catalyzed C-C coupling processes to allow the production of 2-aryl- and 2-alkynyl-substituted cyclopentenones 9-13. SN - 0002-7863 UR - https://www.unboundmedicine.com/medline/citation/17967020/A_general_and_regioselective_synthesis_of_cyclopentenone_derivatives_through_nickel_0__mediated_[3_+_2]_cyclization_of_alkenyl_Fischer_carbene_complexes_and_internal_alkynes_ L2 - https://doi.org/10.1021/ja075106+ DB - PRIME DP - Unbound Medicine ER -