메뉴 건너뛰기




Volumn 41, Issue 26, 2000, Pages 5131-5134

Novel synthesis of chiral terminal allenes via palladium(o)catalyzed reduction of mesylates of 2-bromoalk-2-en-1-ols bearing a protected amino group, using diethylzinc

Author keywords

Allenes; Diethylzinc; Palladium catalysis; Reduction

Indexed keywords

ALKENE DERIVATIVE; ALLENE DERIVATIVE; BROMINE DERIVATIVE; DIETHYLZINC; MESYLIC ACID DERIVATIVE; PALLADIUM;

EID: 0034709579     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00790-5     Document Type: Article
Times cited : (21)

References (35)
  • 22
    • 0001063364 scopus 로고
    • Fox, D. N. A.; Gallagher, T. Tetrahedron 1990, 46, 4697. Fox, D. N. A.; Lathbury, D.; Mahon, M. F.; Molloy, K. C.; Gallagher, T. J. Chem. Soc., Chem. Commun. 1989, 1073. Karstens, W. F. J.; Stol, M.; Rutjes, F. P. J. T.; Hiemstra, H. Synlett 1998, 1126.
    • (1990) Tetrahedron , vol.46 , pp. 4697
    • Fox, D.N.A.1    Gallagher, T.2
  • 24
    • 0001706911 scopus 로고    scopus 로고
    • Fox, D. N. A.; Gallagher, T. Tetrahedron 1990, 46, 4697. Fox, D. N. A.; Lathbury, D.; Mahon, M. F.; Molloy, K. C.; Gallagher, T. J. Chem. Soc., Chem. Commun. 1989, 1073. Karstens, W. F. J.; Stol, M.; Rutjes, F. P. J. T.; Hiemstra, H. Synlett 1998, 1126.
    • (1998) Synlett , pp. 1126
    • Karstens, W.F.J.1    Stol, M.2    Rutjes, F.P.J.T.3    Hiemstra, H.4
  • 26
    • 0000277078 scopus 로고
    • Semmelhack et al. reported that undesired allene was produced by treatment of bromo-mesylate with 2.4 equivalents of a Ni reagent
    • Semmelhack et al. reported that undesired allene was produced by treatment of bromo-mesylate with 2.4 equivalents of a Ni reagent, see: Semmelhack, M. F.; Brickner, S. J. J. Am. Chem. Soc. 1981, 103, 3945.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 3945
    • Semmelhack, M.F.1    Brickner, S.J.2
  • 30
    • 0033531676 scopus 로고    scopus 로고
    • For a report of the palladium-catalyzed reaction of a derivative of 1-oxygenated-2-bromoprop-2-ene
    • For a report of the palladium-catalyzed reaction of a derivative of 1-oxygenated-2-bromoprop-2-ene, see: Trost, B. M.; Oslob, J. D. J. Am. Chem. Soc. 1999, 121, 3057.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 3057
    • Trost, B.M.1    Oslob, J.D.2
  • 31
    • 0008428234 scopus 로고
    • For related works, see: (a)
    • For related works, see: (a) Lukas, J.; Visser, J. P.; Kouwenhoven, A. P. J. Organomet. Chem. 1973, 50, 349; (b) Lupin, M. S.; Powell, J.; Shaw, B. L. J. Chem. Soc. (A) 1966, 1687.
    • (1973) Organomet. Chem. , vol.50 , pp. 349
    • Lukas, J.1    Visser, J.P.2    Kouwenhoven, A.P.J.3
  • 32
    • 37049142586 scopus 로고
    • (b)
    • For related works, see: (a) Lukas, J.; Visser, J. P.; Kouwenhoven, A. P. J. Organomet. Chem. 1973, 50, 349; (b) Lupin, M. S.; Powell, J.; Shaw, B. L. J. Chem. Soc. (A) 1966, 1687.
    • (1966) J. Chem. Soc. (A) , pp. 1687
    • Lupin, M.S.1    Powell, J.2    Shaw, B.L.3
  • 33
    • 0034603478 scopus 로고    scopus 로고
    • While this manuscript was being prepared, an independent report by Bäckvall et al. appeared, describing a reverse reaction of our allene synthesis. Thus, palladium(II)-catalyzed 1,2-oxidation of a certain allene with p-benzoquinone in the presence of LiBr affords, only an isolated example, 2,3-dibromoprop-1-ene derivative
    • While this manuscript was being prepared, an independent report by Bäckvall et al. appeared, describing a reverse reaction of our allene synthesis. Thus, palladium(II)-catalyzed 1,2-oxidation of a certain allene with p-benzoquinone in the presence of LiBr affords, only an isolated example, 2,3-dibromoprop-1-ene derivative, see: Jonasson, C.; Karstens, W. F. J.; Hiemstra, H.; Bäckvall, J.-E. Tetrahedron Lett. 2000, 41, 1619.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 1619
    • Jonasson, C.1    Karstens, W.F.J.2    Hiemstra, H.3    Bäckvall, J.-E.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.