Dihydroxylation and oxidative cleavage of olefins in the presence of sulfur

Tetrahedron Letters

Volumn 37, Issue 26, 1996, Pages 4427-4430

  Sammakia, Tarek ^a   Hurley, T Brian ^a   Sammond, Douglas M ^a   Smith, Randall S ^a   Sobolov, Susan B ^b,c   Oeschger, Thomas R ^b  

^a UNIVERSITY OF COLORADO   (United States)

^b WESLEYAN UNIVERSITY   (United States)

^c PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; SULFUR;

ANALYTIC METHOD; ARTICLE; ELECTRON TRANSPORT; HYDROXYLATION; NONHUMAN; OXIDATION REDUCTION REACTION; REACTION ANALYSIS;

EID: 0030600166     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00879-9     Document Type: Article

References (21)

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3. 2 Stork, G.; van Tamelen, E. E.; Friedman, L. J.; Burgstahler, A. W. J. Am. Chem. Soc. 1953, 75, 394; Djerasi, C.; Engle, R. R. J. Am. Chem. Soc. 1953, 75, 3838; Henbest, H. B.; Khan, S. A. J. Chem. Soc. Chem. Commun. 1968, 1036; Vyas, D. M. ; Hay, C. W. Can. J. Chem. 1975, 53, 1362; Vedejs, E.; McClure, C. K. J. Am. Chem. Soc. 1986, 108, 1094.
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10. We chose to use the protocol described in this paper without added amines since the Sharpless AD procedure, which we have also examined, contains amines, and since Kaldor has shown that sulfide oxidation is accelarated by amines (see ref 3). Warren has reported an achiral ligand accelerated dihydroxylation using quinuclidine which is similar to the Yamamoto procedure. See: Eames, J.; Mitchell, H. J,; Nelson, A.; O'Brien, P.; Warren, S.; Wyatt, P. Tetrahedron Lett., 1995, 36, 1719.
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12. 7 In all cases, authentic samples of products were prepared and used as standards.
13. 4 and concentrated and purified by flash chromatography (hexanes, then 1:1 hexanes / ethyl acetate, then ethyl acetate) to provide the desired diol (46 mg,, 80%).
14. 9 We could not detect any bis-sulfoxides from the dithiane reactions. We suspect that oxidation to the mono-sulfoxide deactivates the remaining sulfide towards further oxidation.
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