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Volumn 17, Issue 14, 2011, Pages 3832-3836

Copper-catalyzed cyclization-fragmentations of enynols

Author keywords

copper; cycloisomerization; fragmentation; gold; rearrangement

Indexed keywords

CYCLOISOMERIZATION; ENYNOLS; FRAGMENTATION; METATHESIS REACTIONS; REARRANGEMENT;

EID: 79952826590     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201002314     Document Type: Article
Times cited : (9)

References (72)
  • 5
    • 79952836581 scopus 로고    scopus 로고
    • Recent reviews on enyne cycloisomerizations: S. P. Nolan, Acc. Chem. Res. 2011, 44, 0000 (DOI:)
    • (2011) Acc. Chem. Res. , vol.44
    • Nolan, S.P.1
  • 56
    • 79952821569 scopus 로고    scopus 로고
    • note
    • Compounds 6 and 7 were obtained from the corresponding aldehyde (HCCMgBr (1.2 equiv), THF, RT (72 %; 6 / 7 =4:1). For determination of the configuration, 6 was transformed in three steps
  • 57
    • 79952858878 scopus 로고    scopus 로고
    • note
    • 2, 0 °C to RT (93 %; 64:36)
  • 58
    • 79952839980 scopus 로고    scopus 로고
    • note
    • major diast.+PhSLi (0.95 equiv), -78 °C to RT (78 % conv.; 56 %)
  • 59
    • 79952820702 scopus 로고    scopus 로고
    • note
    • 2SPh and the propargylic H.
  • 60
    • 79952844183 scopus 로고    scopus 로고
    • note
    • 3 (1.2 equiv), LiCl (1.2 equiv), THF, RT (89 %).
  • 62
    • 79952830723 scopus 로고    scopus 로고
    • note
    • For the absolute configuration of 16, see Ref. [2b]. The absolute configuration of 17 was determined by correlation: 17 was oxidized, the resulting acid esterified and the ester side chain hydrogenated
  • 63
    • 79952851448 scopus 로고    scopus 로고
    • note
    • 2O, 45 °C, 2 h
  • 64
    • 79952859313 scopus 로고    scopus 로고
    • note
    • 2 (1.2 equiv), toluene, 110 °C, 30 min, separation on chiral capillary column (CP-Chirasil-DEX CB (25 m à- 0.25 mm) (Chrompack)): second peak major
  • 66
    • 79952853132 scopus 로고    scopus 로고
    • note
    • 2, RT, 97 %; 3) HCCMgBr (1.2 equiv), THF, RT (53 %+starting ketone (25 %)).
  • 67
    • 79952843943 scopus 로고    scopus 로고
    • note
    • 4 under otherwise identical conditions gave only 14 % of rearranged product and 64 % of starting material.
  • 68
    • 79952837192 scopus 로고    scopus 로고
    • note
    • Compounds 24 and 27 were prepared by addition of the corresponding methyl ketones to propargylmagnesium bromide (1.5 equiv) in THF in 91 and 47 % yield, respectively.
  • 69
    • 79952853706 scopus 로고    scopus 로고
    • note
    • Migration of the cyclopropane C-C bond opposite to the C-Cï£M bond in M (Scheme 7) and P (Scheme 8) leads to the same metathesis product. These reactions proceed via non-classical cations, but for clarity we prefer not to draw partial bonds.
  • 70
    • 0035814401 scopus 로고    scopus 로고
    • For a related early study of platinum-catalyzed metathesis reactions leading to bridged bicyclic systems
    • For a related early study of platinum-catalyzed metathesis reactions leading to bridged bicyclic systems:, A. Fürstner, F. Stelzer, H. Szillat, J. Am. Chem. Soc. 2001, 123, 11863
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 11863
    • Fürstner, A.1    Stelzer, F.2    Szillat, H.3
  • 72
    • 79952840189 scopus 로고    scopus 로고
    • Kindly performed by Professor M. Santelli (University of Aix-Marseille, France)
    • Kindly performed by Professor M. Santelli (University of Aix-Marseille, France).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.