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Volumn 69, Issue 19, 2004, Pages 6478-6481

Formation of a quaternary carbon center through the Pd(0)/PhCOOH-catalyzed allylation of cyclic β-keto esters and 1,3-diketones with alkynes

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CARBON; CARBOXYLIC ACIDS; CATALYSIS; CATALYSTS; ESTERS; PALLADIUM; STEREOCHEMISTRY; TOLUENE;

EID: 4644230134     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0490144     Document Type: Article
Times cited : (51)

References (35)
  • 7
  • 9
    • 0005110907 scopus 로고
    • Graziani, M., Hubert, A. J., Noels, A. F., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands
    • (i) Fiaud, J. C. In Metal-Promoted Selectivity in Organic Synthesis; Graziani, M., Hubert, A. J., Noels, A. F., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1991.
    • (1991) Metal-Promoted Selectivity in Organic Synthesis
    • Fiaud, J.C.1
  • 11
    • 0141630550 scopus 로고    scopus 로고
    • and references therein
    • (a) Kuwano, R.; Uchida, K.; Ito, Y. Org. Lett. 2003, 5, 2177-2179 and references therein.
    • (2003) Org. Lett. , vol.5 , pp. 2177-2179
    • Kuwano, R.1    Uchida, K.2    Ito, Y.3
  • 25
    • 4644340402 scopus 로고    scopus 로고
    • note
    • (a) The reaction of dimethyl methylmalonate with alkynes gave only a trace amount of the adducts even after a prolonged reaction time, although the reaction of methyl malononitrile gave the desired allylation product in high yields.5a
  • 26
    • 4644226476 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra, the methyne proton of methyl malononitrile appears at δ 3.77. On the other hand, the methyne proton of dimethyl methylmalonate and 1a (vide infra) appears at δ 3.44 and 2.30, respectively. This indicates that the methyne proton of methyl malononitrile is more acidic than dimethyl methylmalonate and 1a.
  • 27
    • 4644297615 scopus 로고    scopus 로고
    • note
    • We ran the reaction at higher concentration because we observed that at lower concentrations the reaction became slower.
  • 30
    • 0001349098 scopus 로고
    • Palladium-catalyzed isomerization of alkynes to allenes, see: (a) Sheng, H.; Lin, S.; Huang, Y. Tetrahedron Lett. 1986, 27, 4893-4894.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 4893-4894
    • Sheng, H.1    Lin, S.2    Huang, Y.3
  • 33
    • 0041363231 scopus 로고    scopus 로고
    • and references therein
    • The addition of cyclic β-keto esters to Michael acceptor is known, see: (a) Ooi, T.; Miki, T.; Taniguchi, M.; Shiraishi, M.; Takeuchi, M.; Maruoka, K. Angew. Chem., Int. Ed. 2003, 42, 3796-3798 and references therein. The direct intramolecular addition of cyclic β-keto esters to alkynes and alkenes is known; see:
    • (2003) Angew. Chem., Int. Ed. , vol.42 , pp. 3796-3798
    • Ooi, T.1    Miki, T.2    Taniguchi, M.3    Shiraishi, M.4    Takeuchi, M.5    Maruoka, K.6
  • 34
    • 1842637760 scopus 로고    scopus 로고
    • and references therein
    • The direct intramolecular addition of cyclic β-keto esters to alkynes and alkenes is known; see: (b) Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526-4527 and references therein.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 4526-4527
    • Kennedy-Smith, J.J.1    Staben, S.T.2    Toste, F.D.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.