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Volumn 128, Issue 22, 2006, Pages 7179-7181

Highly regioselective Pd-catalyzed intermolecular aminoacetoxylation of alkenes and evidence for cis-aminopalladation and SN2 C-O bond formation

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DICHLOROETHANE; ACETALDEHYDE; ALKENE; NITROGEN; PALLADIUM; PHTHALIMIDE; SUCCINIMIDE; VINYL ACETATE;

EID: 33744912486     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja061706h     Document Type: Article
Times cited : (372)

References (36)
  • 15
    • 33845551477 scopus 로고
    • For important early studies of stoichiometric Pd-mediated oxyamination of alkenes and related reactions, see: Bäckvall, J.-E. Acc. Chem. Res. 1983, 16, 335-342.
    • (1983) Acc. Chem. Res. , vol.16 , pp. 335-342
    • Bäckvall, J.-E.1
  • 20
    • 32244442435 scopus 로고    scopus 로고
    • The recently discovered Pd-catalyzed dialkoxylation of 2-vinylphenols proceeds by yet another mechanism involving quinone methide intermediates: Schultz, M. J.; Sigman, M. S. J. Am. Chem. Soc. 2006, 128, 1460-1461.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 1460-1461
    • Schultz, M.J.1    Sigman, M.S.2
  • 21
    • 0002858266 scopus 로고    scopus 로고
    • For an exception in which Os-catalyzed aminohydroxylation of styrenes was used to prepare α-aryl amino acids, see: Reddy, K. L.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 1207-1217.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 1207-1217
    • Reddy, K.L.1    Sharpless, K.B.2
  • 22
    • 33744909469 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 23
    • 33744916382 scopus 로고    scopus 로고
    • note
    • Sorensen et al. note that cis-aminopalladation of the alkene is also possible (see footnote 12 in ref 5).
  • 24
    • 33744947403 scopus 로고    scopus 로고
    • note
    • The aldol-based "erythro" designation is used for this compound in conformance with the nomenclature employed in the original characterization of this compound prepared by another method. See Supporting Information for details.
  • 25
    • 0032695063 scopus 로고    scopus 로고
    • Both cis- and trans-heteropalladation of alkenes are possible. See ref 7b, the following examples, and references therein: (a) Hamed, O.; Henry, P. M.; Thompson, C. J. Org. Chem. 1999, 64, 7745-7750.
    • (1999) J. Org. Chem. , vol.64 , pp. 7745-7750
    • Hamed, O.1    Henry, P.M.2    Thompson, C.3
  • 29
    • 0011213911 scopus 로고
    • II-C bonds can occur with retention or inversion. See ref 10, the following selected examples, and references therein: (a) Coulson, D. R. J. Am. Chem. Soc. 1969, 91, 200-202.
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 200-202
    • Coulson, D.R.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.