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Volumn 68, Issue 19, 2003, Pages 7361-7367

Synthesis of antimalarial yingzhaosu A analogues by the peroxidation of dienes with Co(II)/O2/Et3SiH

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COMPOSITION; DERIVATIVES; OXYGEN; SYNTHESIS (CHEMICAL);

EID: 0141789834     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030107f     Document Type: Article
Times cited : (40)

References (49)
  • 16
    • 0029953611 scopus 로고    scopus 로고
    • (d) Bambaoud, T.; Prandi, J. Chem. Commun. 1996, 1229. Furthermore, Magnus and co-workers reported the Mn(III) complex-catalyzed hydroperoxidation of alkenes in the presence of phenylsilane under an oxygen atmosphere: Magnus, P.; Scott, D. A.; Fielding, M. R. Tetrahedron Lett. 2001, 42, 4127.
    • (1996) Chem. Commun. , pp. 1229
    • Bambaoud, T.1    Prandi, J.2
  • 17
    • 0035908267 scopus 로고    scopus 로고
    • (d) Bambaoud, T.; Prandi, J. Chem. Commun. 1996, 1229. Furthermore, Magnus and co-workers reported the Mn(III) complex-catalyzed hydroperoxidation of alkenes in the presence of phenylsilane under an oxygen atmosphere: Magnus, P.; Scott, D. A.; Fielding, M. R. Tetrahedron Lett. 2001, 42, 4127.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 4127
    • Magnus, P.1    Scott, D.A.2    Fielding, M.R.3
  • 18
    • 0029075624 scopus 로고
    • Synthetic application of this methodology: (a) Xu, X.-X.; Dong, H.-Q. J. Org. Chem. 1995, 60, 3039.
    • (1995) J. Org. Chem. , vol.60 , pp. 3039
    • Xu, X.-X.1    Dong, H.-Q.2
  • 30
    • 0004269715 scopus 로고    scopus 로고
    • Applications; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany
    • (f) Boukouvalas, J.; Haynes, R. K. In Radicals in Organic Synthesis; Vol. 2, Applications; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; pp 455-484.
    • (2001) Radicals in Organic Synthesis , vol.2 , pp. 455-484
    • Boukouvalas, J.1    Haynes, R.K.2
  • 37
    • 85088723371 scopus 로고    scopus 로고
    • note
    • 3SiH (4 mmol) in DCE (5 mL) under an oxygen atmosphere for 4 h gave 10-[(triethylsilyl)oxy]decan-2-yl triethylsilyl peroxide (30) (21%) together with 2-[(triethylsilyl)dioxy]decanol (31) (61%). In the absence of the Co(II) catalyst, however, 9-decenol remained intact. (diagram presented).
  • 38
    • 0032809580 scopus 로고    scopus 로고
    • The key intermediate 10 is most likely to be produced by electron transfer from the hydroperoxide 7 to the adventitious Co(III) complexes, followed by deprotonation. Goldstein, S.; Meyerstein, D. Acc. Chem. Res. 1999, 32, 547.
    • (1999) Acc. Chem. Res. , vol.32 , pp. 547
    • Goldstein, S.1    Meyerstein, D.2
  • 39
    • 0141807341 scopus 로고
    • Ando, W., Ed.; Wiley: New York; Chapter 2
    • Spontaneous rearrangement of allyl hydroperoxides via the corresponding peroxy radical is well-known: (a) Porter, N. A. In Organic Peroxides; Ando, W., Ed.; Wiley: New York, 1992; Chapter 2
    • (1992) Organic Peroxides
    • Porter, N.A.1
  • 41
    • 0141584243 scopus 로고    scopus 로고
    • note
    • Compound 20 is most likely to be produced from the corresponding hydroperoxide by an oxygen atom transfer to unidentified reductants. In this respect, hydroperoxides with an electron-withdrawing group at the α-position are well-known to oxidize a variety of compounds such as alkene and sulfide.
  • 46
    • 0141472634 scopus 로고    scopus 로고
    • note
    • In the case of the peroxy radical 22 the activation enthalpy and entropy leading to the formation of the transition state having a chair-chair conformation were calculated as 14.3 kcal/mol and -7.3 cal/mol, respectively.
  • 47
    • 0004104868 scopus 로고
    • de Mayo, P., Ed.; Academic Press: New York; Chapter 4
    • The rate of 5-exo-cyclization of 5-methyl-5-heptenyl radical is known to be ca. 22 times slower than that of 6-methyl-5-heptenyl radical. Beckwith, A. L. J.; Ingold, K. U. In Rearrangements in Ground and Excited States; de Mayo, P., Ed.; Academic Press: New York, 1980; Vol. 1, Chapter 4.
    • (1980) Rearrangements in Ground and Excited States , vol.1
    • Beckwith, A.L.J.1    Ingold, K.U.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.