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Volumn 63, Issue 18, 1998, Pages 6363-6374

Synthesis of Chiral Nitroxides and an Unusual Racemization Reaction

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EID: 0001396250     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9808831     Document Type: Article
Times cited : (46)

References (35)
  • 8
    • 85034483022 scopus 로고    scopus 로고
    • note
    • Although there are several good routes for the synthesis of five-membered ring nitroxides, very few methods exist for the synthesis of six-membered ring chiral nitroxides. See refs 6 and 8.
  • 14
    • 1542741045 scopus 로고
    • German Patent 80,986 (July 14, 1984) from
    • (a) Link, G. German Patent 80,986 (July 14, 1984) from: Chem. Zentr. 1895, 66 (II), 70.
    • (1895) Chem. Zentr. , vol.66 , Issue.2 , pp. 70
    • Link, G.1
  • 19
    • 85034471394 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis.
  • 20
    • 85034475530 scopus 로고    scopus 로고
    • note
    • 3), which corresponds to an ee of ca. 50% based on the optical rotation of enantiomerically pure (+)-29.
  • 21
    • 85034465231 scopus 로고    scopus 로고
    • note
    • The trichloromethyl adduct of indanone was prepared in an effort to avoid the use of base sensitive indanone and to bypass the first step of the mechanism (Figure 2, intermediate 7), but on treatment with mild base it instantly reverted to the indanone, which promptly polymerized.
  • 22
    • 33751154457 scopus 로고
    • 3: (a) Yang, D.; Wong, M.-K.; Yip, Y.-C. J. Org. Chem. 1995, 60, 3887-3889. (b) Murray, R. W.; Singh, M.; Rath, N. Tetrahedron: Asymmetry 1996, 7, 1611-1619.
    • (1995) J. Org. Chem. , vol.60 , pp. 3887-3889
    • Yang, D.1    Wong, M.-K.2    Yip, Y.-C.3
  • 24
    • 85034467613 scopus 로고    scopus 로고
    • note
    • R = 17.3 min (major) and 18.8 min (minor).
  • 25
    • 85034484394 scopus 로고    scopus 로고
    • note
    • R = 17.1 and 18.6 min.
  • 26
    • 85034462891 scopus 로고    scopus 로고
    • note
    • We have not proved that the deoxygenation proceeds without racemization.
  • 30
    • 33847800494 scopus 로고
    • (b) Ganem, B. J. Org. Chem, 1975, 40, 1998-2000.
    • (1975) J. Org. Chem , vol.40 , pp. 1998-2000
    • Ganem, B.1
  • 33
    • 85034466708 scopus 로고    scopus 로고
    • note
    • N-Oxo ammonium salt 49 oxidizes i-PrOH to acetone. The resulting hydroxylamine is oxidized by a further 1 equiv of 49 to give nitroxide 43.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.