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Volumn 40, Issue 12, 1984, Pages 2247-2255

On stereochemistry of osmium tetraoxide oxidation of allylic alcohol systems. Empirical rule

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EID: 33748632563     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(84)80008-3     Document Type: Article
Times cited : (478)

References (45)
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    • Osmium tetraoxide cis hydroxylation of unsaturated substrates
    • For a recent review on osmium tetroxide oxidation, see
    • (1980) Chemical Reviews , vol.80 , pp. 187
    • Schroder1
  • 19
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    • 4, oxidation of 3-methyl-3-hydroxy-l-cyclohexene gave a ca 1:1 mixture of two possible products.
  • 20
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    • Unlike the acyclic systems, acyl groups are effective in directing stereoselective osmylation. For example, 2-cyclohexen-l-ol acetate yielded 1β-acetoxy-2α, 3α-dihydroxycyclohexane as the major product with the comparable stereoselectivity with the 2-cyclohexen-l-ol.
  • 22
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    • 4 oxidation of α,β -unsaturated carbonyl compounds. We thank him for the preprint of the work
    • (1993) Tetrahedron Letters , vol.37 , pp. 3951
    • Stork1    Kahn2
  • 24
    • 2742572537 scopus 로고
    • Synthesis of 8-deoxy-D-erythro-D-galacto-octose. Determination of the configuration of two octenoses
    • Many examples known in the literature are consistent with this formulation. For example, see an example reported by
    • (1969) Canadian Journal of Chemistry , vol.47 , pp. 2871
    • Lance1    Szarek2    Jones3    Howarth4
  • 25
    • 84918062253 scopus 로고    scopus 로고
    • 4, oxidation of diene 46 yielded arabinose, but not ribose. Assuming permanganate oxidation takes place on the diene system in a stepwise fashion, the stereochemical outcome of permanganate oxidation was opposite to that predicted for osmium tetroxide oxidation.
  • 26
    • 0021088156 scopus 로고
    • Such an example has recently been reported by Prof. Danishefsky at the Gordon Research Conf. on Nat. Prod- ucts, New Hampton, New Hampshire, Aug. 1983. We thank him for the preprint of the work
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 6715
    • Larson1    Danishefsky2
  • 29
    • 84918062252 scopus 로고    scopus 로고
    • This ratio is based on the amount of product(s) isolated by crystallization.
  • 30
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    • W.J. Christ, J.K. Cha Y. Kishi, unpublished results.
  • 31
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    • S.S. K.O, M. Yonaga and Y. Kishi, unpublished results.
  • 33
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    • S.H. Kang, W.W. McWhorter, Jr. Y. Kishi, unpublished results.
  • 38
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    • H. Fujioka Y. Kishi, unpublished results.
  • 40
    • 84987284907 scopus 로고
    • Recherches dans la s�rie des cyclitols, XLI. Synth�ses de deux cyclopentane-pentols
    • 4 oxidation of poly- hydroxycyclopentenes, and refs cit
    • (1970) Helvetica Chimica Acta , vol.53 , pp. 2288
  • 41
    • 0011801752 scopus 로고
    • Total Synthesis of 4-O-Methyl-DL-lyxose and 4-Deoxy-DL-ribose. Further Evidence of the Stereoselective Hydroxylation of Double Bonds by Osmic Acid
    • (1971) Canadian Journal of Chemistry , vol.49 , pp. 1339
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  • 42
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    • Studies on the Synthesis of Novel Carbohydrates with Sulfur in the Ring. Part III. The Synthesis of Derivatives of 2,6-Dithio-hex-4-en-2-ulopyranosidononitriles
    • (1975) Canadian Journal of Chemistry , vol.53 , pp. 1362
    • Vyas1    Hay2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.