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Volumn 129, Issue 4, 2007, Pages 762-763

A facile Pd(0)-catalyzed regie- and stereoselective diamination of conjugated dienes and trienes

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; PALLADIUM; TRIENE; UNCLASSIFIED DRUG;

EID: 33846624362     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0680562     Document Type: Article
Times cited : (226)

References (32)
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    • For leading references on recent Ritter-type diamination see: a
    • For leading references on recent Ritter-type diamination see: (a) Li, G.; Kim, S. H.; Wei, H-X. Tetrahedron Lett. 2000, 41, 8699.
    • (2000) Tetrahedron Lett , vol.41 , pp. 8699
    • Li, G.1    Kim, S.H.2    Wei, H.-X.3
  • 6
    • 33847087811 scopus 로고    scopus 로고
    • For examples of metal-mediated diaminations, see the following. Co: (a) Becker, P. N, White, M. A, Bergman, R. G. J. Am. Chem. Soc. 1980, 102, 5676
    • For examples of metal-mediated diaminations, see the following. Co: (a) Becker, P. N.; White, M. A.; Bergman, R. G. J. Am. Chem. Soc. 1980, 102, 5676.
  • 14
    • 23844527400 scopus 로고    scopus 로고
    • For a recent Cu(II)-mediated intramolecular diamination, see: Zabawa, T. P.; Kasi, D.; Chemler, S. R. J. Am. Chem. Soc. 2005, 127, 11250.
    • For a recent Cu(II)-mediated intramolecular diamination, see: Zabawa, T. P.; Kasi, D.; Chemler, S. R. J. Am. Chem. Soc. 2005, 127, 11250.
  • 15
    • 0035915127 scopus 로고    scopus 로고
    • 2 see: (a) Li, G.; Wei, H.-X.; Kim, S. H.; Carducci, M. D. Angew. Chem., Int. Ed. 2001, 40, 4277.
    • 2 see: (a) Li, G.; Wei, H.-X.; Kim, S. H.; Carducci, M. D. Angew. Chem., Int. Ed. 2001, 40, 4277.
  • 19
    • 0000518357 scopus 로고
    • For leading reviews, see: a
    • For leading reviews, see: (a) Hegedus, L. S. Tetrahedron 1984, 40, 2415.
    • (1984) Tetrahedron , vol.40 , pp. 2415
    • Hegedus, L.S.1
  • 22
    • 33846569041 scopus 로고    scopus 로고
    • For examples of less common cis-aminopalladation, see: (a) Isomura, K, Okada, N, Saruwatari, M, Yamasaki, H, Taniguchi, H, Chem. Lett. 1985, 385
    • For examples of less common cis-aminopalladation, see: (a) Isomura, K.; Okada, N.; Saruwatari, M.; Yamasaki, H.; Taniguchi, H.; Chem. Lett. 1985, 385.
  • 26
    • 0042401093 scopus 로고    scopus 로고
    • Prepared on the basis of the reported method: Greene, F. D.; Stowell, J. C.; Bergmark, W. R. J. Org. Chem. 1969, 34, 2254.
    • Prepared on the basis of the reported method: Greene, F. D.; Stowell, J. C.; Bergmark, W. R. J. Org. Chem. 1969, 34, 2254.
  • 27
    • 0003593740 scopus 로고
    • For a leading review on diaziridinones, see:, Hassner, A, Ed, John Wiley & Sons, Inc: New York
    • For a leading review on diaziridinones, see: Heine, H. W. In The Chemistry of Heterocyclic Compounds; Hassner, A., Ed.; John Wiley & Sons, Inc: New York, 1983; pp 547.
    • (1983) The Chemistry of Heterocyclic Compounds , pp. 547
    • Heine, H.W.1
  • 28
    • 33846589403 scopus 로고    scopus 로고
    • 1H NMR of the crude reaction mixture if there was any.
    • 1H NMR of the crude reaction mixture if there was any.
  • 29
    • 33846629097 scopus 로고    scopus 로고
    • When isoprene was used, however, a mixture of two regioisomers (2.3: 1) was formed in 90% yield after 1 h reaction. The diamination slightly preferred the more substituted double bond in this case.
    • When isoprene was used, however, a mixture of two regioisomers (2.3: 1) was formed in 90% yield after 1 h reaction. The diamination slightly preferred the more substituted double bond in this case.
  • 30
    • 0032864417 scopus 로고    scopus 로고
    • The insertion of Ni and Pd to the N-N bond of diaziridinone has been reported, see: Komatsu, M.; Tamabuchi, S.; Minakata, S.; Ohshiro, Y. Heterocycles 1999, 50, 67. However, to the best our knowledge, the reaction of the resulting complex 10 with an olefin has not been reported.
    • The insertion of Ni and Pd to the N-N bond of diaziridinone has been reported, see: Komatsu, M.; Tamabuchi, S.; Minakata, S.; Ohshiro, Y. Heterocycles 1999, 50, 67. However, to the best our knowledge, the reaction of the resulting complex 10 with an olefin has not been reported.
  • 31
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    • For a recent leading review on π-allyl Pd chemistry, see
    • For a recent leading review on π-allyl Pd chemistry, see: Trost, B. M. J. Org. Chem. 2004, 69, 5813.
    • (2004) J. Org. Chem , vol.69 , pp. 5813
    • Trost, B.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.