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Volumn 65, Issue 33, 2009, Pages 6648-6655

New synthetic strategies for the stereocontrolled synthesis of substituted 'skipped' diepoxides

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKYNE; BROMIDE; EPOXIDE; PALLADIUM;

EID: 67650269817     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.05.074     Document Type: Article
Times cited : (9)

References (83)
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    • The bond dissociation energy of the doubly allylic C-H bonds in 1,4-pentadiene is quite low; it has been measured at 68.5 kcal/mol. See:
    • The bond dissociation energy of the doubly allylic C-H bonds in 1,4-pentadiene is quite low; it has been measured at 68.5 kcal/mol. See:. McMahon T.B., and Kebarle P. J. Am. Chem. Soc. 96 (1974) 5940
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 5940
    • McMahon, T.B.1    Kebarle, P.2
  • 20
    • 67650275167 scopus 로고    scopus 로고
    • note
    • In Scheme 1, distal Me groups are shown in red and proximal in blue, for clarity.
  • 21
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    • For examples of highly endo-regioselective intramolecular opening of distally Me-substituted epoxides under acidic conditions, see
    • For examples of highly endo-regioselective intramolecular opening of distally Me-substituted epoxides under acidic conditions, see:
  • 27
    • 67650278566 scopus 로고    scopus 로고
    • For a canonical example of highly exo-regioselective intramolecular opening of proximally Me-substituted epoxides under acidic conditions, see
    • For a canonical example of highly exo-regioselective intramolecular opening of proximally Me-substituted epoxides under acidic conditions, see:
  • 34
    • 67650275894 scopus 로고    scopus 로고
    • A racemic synthesis of 4 was reported by Bowman and McDonald:
    • A racemic synthesis of 4 was reported by Bowman and McDonald:
  • 36
    • 67650271868 scopus 로고    scopus 로고
    • (+)-4, the enantiomer of 4, has been prepared by the Nakata group:
    • (+)-4, the enantiomer of 4, has been prepared by the Nakata group:
  • 38
    • 0001032404 scopus 로고    scopus 로고
    • A previous asymmetric synthesis of 4 by the Jamison group is reported in Ref. 10a. We report a streamlined gram-scale synthesis of 4, requiring five steps from 2,3-dihydropyran, in Supplementary data to Ref. 14
    • Suzuki K., and Nakata T. Org. Lett. 4 (2002) 2739 A previous asymmetric synthesis of 4 by the Jamison group is reported in Ref. 10a. We report a streamlined gram-scale synthesis of 4, requiring five steps from 2,3-dihydropyran, in Supplementary data to Ref. 14
    • (2002) Org. Lett. , vol.4 , pp. 2739
    • Suzuki, K.1    Nakata, T.2
  • 39
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    • Initial report
    • Initial report:
  • 41
    • 67650256647 scopus 로고    scopus 로고
    • Successful carbometallation in the presence of free hydroxyl groups
    • Successful carbometallation in the presence of free hydroxyl groups:
  • 43
    • 67650271864 scopus 로고    scopus 로고
    • Recent review
    • Recent review:
  • 47
    • 67650275570 scopus 로고    scopus 로고
    • For a general review of the 1,2-difunctionalization of alkynes via metallometalation, see
    • For a general review of the 1,2-difunctionalization of alkynes via metallometalation, see:
  • 49
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    • For a recent review of silylcupration, see
    • For a recent review of silylcupration, see:
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    • For a recent review of stannylcupration, see
    • For a recent review of stannylcupration, see:
  • 55
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    • For a few examples of the manifold potential electrophilic quenches and transmetalation possibilities open to alkenylaluminum and alkenylcopper species, including conjugated additions, transmetalation to Pd, and subsequent cross-coupling, see
    • For a few examples of the manifold potential electrophilic quenches and transmetalation possibilities open to alkenylaluminum and alkenylcopper species, including conjugated additions, transmetalation to Pd, and subsequent cross-coupling, see:
  • 67
    • 67650276586 scopus 로고    scopus 로고
    • note
    • 3 was found to improve yield slightly. Remarkably, a trace of silyl ether cleavage was observed in the absence of this base, presumably due to a small quantity of HBr in solution.
  • 68
    • 67650278380 scopus 로고    scopus 로고
    • For discussions of improving the stereoselectivity and reactivity of cross metatheses, see
    • For discussions of improving the stereoselectivity and reactivity of cross metatheses, see:
  • 71
    • 67650277326 scopus 로고    scopus 로고
    • For a recent review, see
    • For a recent review, see:
  • 79
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    • For an overview of the bulky, electron-rich biaryl phosphines developed by the Buchwald group, see
    • For an overview of the bulky, electron-rich biaryl phosphines developed by the Buchwald group, see:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.