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Volumn 129, Issue 48, 2007, Pages 14866-14867

Palladium-catalyzed synthesis of spiro[2.4]heptanes: Ligand-dependent position control in the nucleophilic attack to a π-allylpalladium intermediate

Author keywords

[No Author keywords available]

Indexed keywords

HEPTANE DERIVATIVE; PALLADIUM; SPIRO[2.4]HEPTANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 36849007542     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja077236o     Document Type: Article
Times cited : (93)

References (39)
  • 1
    • 0003995267 scopus 로고    scopus 로고
    • For recent reviews, see: (a) Negishi, E, Ed, John Wiley & Sons: Hoboken, NJ
    • For recent reviews, see: (a) Negishi, E., Ed. Handbook of Organopalladium Chemistry for Organic Synthesis; John Wiley & Sons: Hoboken, NJ, 2002; Vol. 2.
    • (2002) Handbook of Organopalladium Chemistry for Organic Synthesis , vol.2
  • 15
    • 0000752177 scopus 로고    scopus 로고
    • For examples of obtaining cyclopropanes as a minor product in the palladium-catalyzed allylic alkylation, see: (a) Carfagna, C, Mariani, L, Musco, A, Sallese, G, Santi, R. J. Org. Chem. 1991, 56, 3924
    • For examples of obtaining cyclopropanes as a minor product in the palladium-catalyzed allylic alkylation, see: (a) Carfagna, C.; Mariani, L.; Musco, A.; Sallese, G.; Santi, R. J. Org. Chem. 1991, 56, 3924.
  • 18
    • 33845470366 scopus 로고    scopus 로고
    • For examples of the use of other transition metals involving a nucleophilic attack to the central carbon of a π-allylmetal species, see: (a) Periana, R. A, Bergman, R. G. J. Am. Chem. Soc. 1984, 106, 7272
    • For examples of the use of other transition metals involving a nucleophilic attack to the central carbon of a π-allylmetal species, see: (a) Periana, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1984, 106, 7272.
  • 24
    • 36849055230 scopus 로고    scopus 로고
    • The relative configuration of the major diastereomer of 4ea (entry 5) was determined by X-ray crystallographic analysis (see Supporting Information).
    • The relative configuration of the major diastereomer of 4ea (entry 5) was determined by X-ray crystallographic analysis (see Supporting Information).
  • 25
    • 36849043270 scopus 로고    scopus 로고
    • The relative configuration of the minor diastereomer of 4ae (entry 9) was determined by X-ray crystallographic analysis (see Supporting Information).
    • The relative configuration of the minor diastereomer of 4ae (entry 9) was determined by X-ray crystallographic analysis (see Supporting Information).
  • 30
    • 8744240568 scopus 로고    scopus 로고
    • For leading references, see: a
    • For leading references, see: (a) Burger, E. C.; Tunge, J. A. Org. Lett. 2004, 6, 4113.
    • (2004) Org. Lett , vol.6 , pp. 4113
    • Burger, E.C.1    Tunge, J.A.2
  • 36
    • 36849072752 scopus 로고    scopus 로고
    • The relative configuration of the major diastereomer of 3aa was determined by X-ray crystallographic analysis of its carboxylic acid derivative (see Supporting Information).
    • The relative configuration of the major diastereomer of 3aa was determined by X-ray crystallographic analysis of its carboxylic acid derivative (see Supporting Information).
  • 37
    • 36849010359 scopus 로고    scopus 로고
    • For relevant discussions on the cyclopropanation versus allylation, see: (a) ref 4b
    • For relevant discussions on the cyclopropanation versus allylation, see: (a) ref 4b.
  • 39
    • 36849044846 scopus 로고    scopus 로고
    • As kindly suggested by one of the reviewers, the observed selectivity may be explained by the steric demand of palladacyclobutane intermediate C (Figure 2), the formation of which becomes unfavorable upon using a bulky phosphine ligand.
    • As kindly suggested by one of the reviewers, the observed selectivity may be explained by the steric demand of palladacyclobutane intermediate C (Figure 2), the formation of which becomes unfavorable upon using a bulky phosphine ligand.


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