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Volumn , Issue 17, 2008, Pages 2605-2608

Lewis acid induced highly regioselective synthesis of a new class of substituted isoxazolidines

Author keywords

Addition reactions; Isoxazolidine; Lewis acids; Oxime; Regioselectivity

Indexed keywords

ACETOACETIC ACID DERIVATIVE; ALKYLIDENE ACETOACETATE DERIVATIVE; HYDROXYLAMINE; ISOXAZOLIDINE DERIVATIVE; LEWIS ACID; N,O BIS(TRIMETHYLSILYL)HYDROXYLAMINE; UNCLASSIFIED DRUG;

EID: 55449124802     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-0028-1083520     Document Type: Article
Times cited : (11)

References (55)
  • 15
    • 0001587733 scopus 로고
    • For previous examples of alkylhydroxylamine addition to unsaturated derivatives, see: e
    • For previous examples of alkylhydroxylamine addition to unsaturated derivatives, see: (e) Baldwin, S. W.; Aube, J. Tetrahedron Lett. 1987, 28, 179.
    • (1987) Tetrahedron Lett , vol.28 , pp. 179
    • Baldwin, S.W.1    Aube, J.2
  • 24
    • 11544346529 scopus 로고    scopus 로고
    • Isoxazolidines may be readily obtained via enantioselective 1,3-dipolar cycloaddition of nitrones to alkenes. For recent papers, see: (a) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863.
    • Isoxazolidines may be readily obtained via enantioselective 1,3-dipolar cycloaddition of nitrones to alkenes. For recent papers, see: (a) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863.
  • 37
  • 49
    • 34248562794 scopus 로고    scopus 로고
    • The anomers of 3,4-trans-3a could not be separated by flash chromatography and their stereochemistry was attributed on the basis of the coupling constants and through NOE experiments. The major anomer showed that the methyl group at 5-position was cis to the proton at C4. For NMR determination of similar structures, see: (a) Yong, S. R.; Ung, A. T.; Pyne, S. G.; Skelton, B. W.; White, A. H. Tetrahedron 2007, 63, 5579.
    • The anomers of 3,4-trans-3a could not be separated by flash chromatography and their stereochemistry was attributed on the basis of the coupling constants and through NOE experiments. The major anomer showed that the methyl group at 5-position was cis to the proton at C4. For NMR determination of similar structures, see: (a) Yong, S. R.; Ung, A. T.; Pyne, S. G.; Skelton, B. W.; White, A. H. Tetrahedron 2007, 63, 5579.
  • 52
    • 55449134853 scopus 로고    scopus 로고
    • 3a: Major anomer: 1H NMR (600 MHz, C6D 6, δ, 0.82 (d, 3 H, J, 6.6 Hz, 0.93 (t, 3 H, J, 7.2 Hz, 0.97 (d, 3 H, J, 6.6 Hz, 1.51 (s, 3 H, 1.64 (m, 1 H, 2.83 (d, 1 H, J, 5.4 Hz, 3.58 (dd, 1 H, J, 5.4, 7.2 Hz, 3.93 (m, 1 H, 3.98 (m, 1 H, 13C NMR (75 MHz, CDCl3, 5= 14.1, 18.7, 19.4, 23.8, 32.6, 60.1, 61.3, 67.9, 106.5, 170.7. Minor anomer: 1H NMR (600 MHz, C6D6, δ, 0.86 (d, 3 H, J, 7.2 Hz, 0.88 (d, 3 H, J, 6.6 Hz, 0.91 (t, 3 H, J, 7.2 Hz, 1.45 (s, 3 H, 1.50 (m, 1 H, 3.03 (d, 1 H, J, 7.8 Hz, 3.88 (dd, 1 H, J, 7.2, 7.8 Hz, 3.92 (m, 2 H, 13C NMR 75 MHz, CDCl3, δ, 14.2, 19.6, 20.4, 22.2, 30.1, 61.1, 62.0, 71.9, 108.4, 171.5
    • 3): δ = 14.2, 19.6, 20.4, 22.2, 30.1, 61.1, 62.0, 71.9, 108.4, 171.5.
  • 53
    • 55449125318 scopus 로고    scopus 로고
    • 3): δ = 10.6, 14.1, 22.4, 29.4, 61.0, 131.3, 143.9, 154.4, 167.5.
    • 3): δ = 10.6, 14.1, 22.4, 29.4, 61.0, 131.3, 143.9, 154.4, 167.5.
  • 54
    • 55449126233 scopus 로고    scopus 로고
    • 3): δ = 14.0, 17.6, 18.7, 25.1, 33.3, 37.6, 61.0, 61.6, 65.1, 109.8, 167.5.
    • 3): δ = 14.0, 17.6, 18.7, 25.1, 33.3, 37.6, 61.0, 61.6, 65.1, 109.8, 167.5.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.