메뉴 건너뛰기




Volumn 6, Issue 23, 2004, Pages 4303-4306

Oxidative rearrangement of cyclic tertiary allylic alcohols with IBX in DMSO

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE;

EID: 9444236739     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048210u     Document Type: Article
Times cited : (74)

References (41)
  • 1
    • 0011947007 scopus 로고
    • Trost, B. M., Fleming, I., Ley, S. V., Eds.; Pergamon: Oxford
    • Schlecht, M. F. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Ley, S. V., Eds.; Pergamon: Oxford, 1991; Vol. 7, pp 815-837.
    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 815-837
    • Schlecht, M.F.1
  • 10
    • 0000667298 scopus 로고
    • and references therein
    • (f) Luzzio, F. A.; Moor, W. J. J. Org. Chem. 1993, 58, 2966 and references therein.
    • (1993) J. Org. Chem. , vol.58 , pp. 2966
    • Luzzio, F.A.1    Moor, W.J.2
  • 12
    • 0003122611 scopus 로고    scopus 로고
    • For a recent review on an oxochromium(VI)-based oxidant, see: Luzzio, F. A. Org. React. 1998, 53, 1.
    • (1998) Org. React. , vol.53 , pp. 1
    • Luzzio, F.A.1
  • 13
    • 1542642335 scopus 로고
    • For an eminent review on chromium-catalyzed oxidations, see: Muzart, J. Chem. Rev. 1992, 92, 113. See also: Riahi, A.; Hénin, F.; Muzart, J. Tetrahedron Lett. 1999, 40, 2303.
    • (1992) Chem. Rev. , vol.92 , pp. 113
    • Muzart, J.1
  • 14
    • 0033582968 scopus 로고    scopus 로고
    • For an eminent review on chromium-catalyzed oxidations, see: Muzart, J. Chem. Rev. 1992, 92, 113. See also: Riahi, A.; Hénin, F.; Muzart, J. Tetrahedron Lett. 1999, 40, 2303.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 2303
    • Riahi, A.1    Hénin, F.2    Muzart, J.3
  • 15
    • 85039464586 scopus 로고    scopus 로고
    • note
    • Oxidative rearrangement can also go through an allylic cation generated by solvolysis of the chromate ester, as similarly described in Scheme 4 (vide infra). See also ref 4.
  • 20
    • 9444221234 scopus 로고    scopus 로고
    • Schmalz, H.-G., Wirth, T., Eds.: Wiely-VCH: Weiheim
    • (e) Wirth, T. In Organic Synthesis Highlights V; Schmalz, H.-G., Wirth, T., Eds.: Wiely-VCH: Weiheim, 2003; pp 144-150.
    • (2003) Organic Synthesis Highlights V , pp. 144-150
    • Wirth, T.1
  • 25
    • 85039484450 scopus 로고    scopus 로고
    • note
    • We reasoned that the carboxy group imparts considerable solubility in DMSO and suitable acidity to IBX.
  • 31
    • 0038655020 scopus 로고
    • PhIO has been found to oxidize various alcohols to carbonyl compounds in refluxing dioxane; see: Takaya, T.; Enyo, H.; Imoto. E. Bull. Chem. Soc., Jpn. 1968, 41, 1032.
    • (1968) Bull. Chem. Soc., Jpn. , vol.41 , pp. 1032
    • Takaya, T.1    Enyo, H.2    Imoto, E.3
  • 32
    • 85039469207 scopus 로고    scopus 로고
    • note
    • 4 and concentrated in vacuo. The remaining residue was purified by column chromatography on silica gel to give 85% of 1b.
  • 33
    • 85039463452 scopus 로고    scopus 로고
    • note
    • (16) Addition of pyridine had unpredictable results. For example, it suppressed the dehydration of 1a and decreased the yield of 1b to 70% due to the contamination of dark-brown byproducts derived from pyridine.
  • 40
    • 0037070617 scopus 로고    scopus 로고
    • Addition of a radical inhibitor, galvinoxyl, did not affect the IBX-mediated oxidative rearrangement of 1a, suggesting that the reaction does not involve discrete radical intermediates. Cf.: Nicolaou, K. C.; Baran, P. S.; Zhong, Y.-L.; Sugita, K. J. Am. Chem. Soc. 2002, 124, 2212.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 2212
    • Nicolaou, K.C.1    Baran, P.S.2    Zhong, Y.-L.3    Sugita, K.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.