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Volumn 71, Issue 4, 2006, Pages 1569-1575

Metal-catalyzed oxidation and epoxidation of α-hydroxy vinyl and dienyl sulfoxides

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATES; CATALYSIS; OXIDATION; STEREOCHEMISTRY;

EID: 33644524966     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052244d     Document Type: Article
Times cited : (24)

References (54)
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    • For a review on the preparation and applications of α-oxy sulfones, including sulfonyl oxiranes, see: (a) Chemla, F. J. Chem. Soc., Perkin Trans. 1 2002, 275-299. For
    • (2002) J. Chem. Soc., Perkin Trans. 1 , pp. 275-299
    • Chemla, F.1
  • 6
    • 85034475814 scopus 로고
    • other reviews on aspects of the synthesis and reactivity of sulfinyl and sulfonyl oxiranes, see: (b) Satoh, T.; Yamakawa, K. Synlett 1992, 455-468.
    • (1992) Synlett , pp. 455-468
    • Satoh, T.1    Yamakawa, K.2
  • 7
    • 0001318042 scopus 로고    scopus 로고
    • (c) Satoh, T. Chem. Rev. 1996, 96, 3303-3325.
    • (1996) Chem. Rev. , vol.96 , pp. 3303-3325
    • Satoh, T.1
  • 8
    • 0035861708 scopus 로고    scopus 로고
    • For recent references on applications of sulfinyl and sulfonyl oxiranes, see: (d) Mori, Y.; Hayashi, H. J. Org. Chem. 2001, 66, 8666-8668.
    • (2001) J. Org. Chem. , vol.66 , pp. 8666-8668
    • Mori, Y.1    Hayashi, H.2
  • 13
    • 0037430676 scopus 로고    scopus 로고
    • For a recent application of these building blocks within synthetic studies toward yessotoxin and adriatoxin, see: Mori, Y.; Takase, T.; Noyori, R. Tetrahedron Lett. 2003, 44, 2319-2322.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 2319-2322
    • Mori, Y.1    Takase, T.2    Noyori, R.3
  • 15
    • 24944439529 scopus 로고    scopus 로고
    • (k) For an application to the synthesis of a fragment of gambierol, see: Furuta, H.; Hase, M.; Noyori, R.; Mori, Y. Org. Lett. 2005, 7, 4061-4064.
    • (2005) Org. Lett. , vol.7 , pp. 4061-4064
    • Mori, Y.1
  • 16
    • 0027278828 scopus 로고
    • For reviews on the synthesis of carbohydrate derivatives from acyclic precursors, see: (a) Ager, D. J.; East, M. B. Tetrahedron 1993, 49, 5683-5765.
    • (1993) Tetrahedron , vol.49 , pp. 5683-5765
    • Ager, D.J.1    East, M.B.2
  • 32
    • 33644550453 scopus 로고    scopus 로고
    • note
    • At long reaction times, other products, not fully identified, presumably derived from overoxidation were obtained.
  • 45
    • 0001072616 scopus 로고
    • Interestingly, hindered isopropylidenedioxy ribose acetates are allylated under similar conditions, see: Wilcox, C. S.; Otoski, R. M. Tetrahedron Lett. 1986, 27, 1011-1014.
    • (1986) Tetrahedron Lett. , vol.27 , pp. 1011-1014
    • Wilcox, C.S.1    Otoski, R.M.2
  • 50
  • 52
    • 33644560137 scopus 로고    scopus 로고
    • note
    • The stereochemistry of the new chiral center is assigned tentatively in analogy with the results of Procter for nucleophilic additions to α,β-epoxy aldehydes. See ref 17b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.