Highly chemoselective osmium-mediated dihydroxylation of 2-vinyl and 2- allyl-1, 3-dithiane 1-oxides

Tetrahedron

Volumn 54, Issue 48, 1998, Pages 14581-14596

  Page, Philip C Bulman ^a   McKenzie, Michael J ^a   Buckle, Derek R ^a,b  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

OSMIUM;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROXYLATION; OXIDATION; PRIORITY JOURNAL;

EID: 0032569847     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00923-5     Document Type: Article

References (23)

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2. 1 Criegee, R. Justus Liebigs Ann. Chem., 1936, 522, 75; Criegee, R; Marchand, B.;Wannowius, H. Jusfus Liebigs Ann. Chem., 1942, 550, 99; Schroder, M. Chem, Rev., 1980, 80, 187.
3. 1 Criegee, R. Justus Liebigs Ann. Chem., 1936, 522, 75; Criegee, R; Marchand, B.;Wannowius, H. Jusfus Liebigs Ann. Chem., 1942, 550, 99; Schroder, M. Chem, Rev., 1980, 80, 187.
4. 2 Van Rheenan, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett., 1976, 1973; Sharpless, K. B.; Akashi, K. J. Am. Chem. Soc., 1976, 98, 1986.
5. 2 Van Rheenan, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett., 1976, 1973; Sharpless, K. B.; Akashi, K. J. Am. Chem. Soc., 1976, 98, 1986.
6. 3 Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K,-S.; Kwong, H,-L.; Morikawa, K. Wang, Z,-M.; Xu, D.; Zhang, X,-L. J. Org. Chem., 1992, 57, 2768; Kolb, H. C.; Van Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev., 1994, 94, 2483. Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed., VCH Publishers Inc.: New York, 1993; pp. 227-272.
7. 3 Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K,-S.; Kwong, H,-L.; Morikawa, K. Wang, Z,-M.; Xu, D.; Zhang, X,-L. J. Org. Chem., 1992, 57, 2768; Kolb, H. C.; Van Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev., 1994, 94, 2483. Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed., VCH Publishers Inc.: New York, 1993; pp. 227-272.
8. 3 Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K,-S.; Kwong, H,-L.; Morikawa, K. Wang, Z,-M.; Xu, D.; Zhang, X,-L. J. Org. Chem., 1992, 57, 2768; Kolb, H. C.; Van Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev., 1994, 94, 2483. Sharpless, K. B. In Catalytic Asymmetric Synthesis; Ojima, I., Ed., VCH Publishers Inc.: New York, 1993; pp. 227-272.
9. 4 Page, P. C. B.; McKenzie, M. J.; Allin, S. M.; Klair, S. S.; Buckle, D. Tetrahedron, 1997, 51, 13149, and references contained therein.
10. 5 Page, P. C. B.; Wilkes, R. D.; Witty, M. J. Org. Prep. Proc. Intl., 1994, 26, 702. and references contained therein.
11. 6 Syn and anti refer to the relationship between the sulfoxide and alkenyl moieties. The structure of 2b was confirmed by single crystal X-ray crystallography. The relative stereochemistry of other sulfoxides was assigned by correlation of 1H NMR and TLC evidence. The 1H NMR signal corresponding to the dithiane 2-position alkyl group in the anti diastereoisomer always appears downfield of that of the syn diastereoisomer. The syn diastereoisomer is always less polar upon TLC analysis than is the anti diastereoisomer.
12. 7 Maycock, C. D.; Afonso, C. A. M.; Barros, M. T.; Godinho, L. S. Synthesis, 1991, 575.
13. 8 Seebach, D.;Kolb, M.; Gröbel, B.-T. Chem. Ber., 1973, 106, 2277; Seebach, D.;Kolb, M.; Gröbel, B.-T. Tetrahedron Lett., 1974, 36, 3171.
14. 8 Seebach, D.;Kolb, M.; Gröbel, B.-T. Chem. Ber., 1973, 106, 2277; Seebach, D.;Kolb, M.; Gröbel, B.-T. Tetrahedron Lett., 1974, 36, 3171.
15. 9 Page, P. C. B.; Purdie, M.; Lathbury, D. Tetrahedron, 1997, 51, 1061.
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17. 10 Solladié, G.; Fréchou, C.; Demailly, G. Tetrahedron Lett, 1986, 27, 2867. Hauser, F. M.; Ellenberger, S. R. J. Am. Chem. Soc., 1984, 25, 2458.
18. 11 Kaldor, S. W.; Hammond, M. Tetrahedron Lett, 1991, 32, 5043; Priebe, W.; Grynkiewicz, G. Tetrahedron Lett., 1991, 32, 7353.
19. 11 Kaldor, S. W.; Hammond, M. Tetrahedron Lett, 1991, 32, 5043; Priebe, W.; Grynkiewicz, G. Tetrahedron Lett., 1991, 32, 7353.
20. 12 Walsh, P. J.; Ho, P. T.; King, S. B,; Sharpless, K. B. Tetrahedron Lett., 1994, 35, 5129.
21. 13 Eames, J.; Mitchell, H. J.; Nelson, A.; O'Brien, P.; Warren, S.; Wyatt, P. Tetrahedron Lett., 1995, 36, 1719.
22. 14 For the structural assignment of major and minor diastereoisomers of products, single crystal X-ray analysis was conducted on 10e, 11a, 11c, 13c, and 13e (entry nos. 1, 3, 5, 8, 10). The reactions giving 12/13b and 12/13d (entry nos. 7, 9) are unselective, the 12/13b mixture proved inseparable. All attempts to obtain suitable crystals of the remaining compounds (10/11b, 10/11d and 12/13a) (entry nos. 2, 4, 6) proved unsuccessful. Several derivatives of these compounds were prepared, including mono-benzyl ethers, mono-trityl ethers, cyclic carbonates, di-acetates and aldehydes, but none proved to be crystalline. There is no discernible pattern in the NMR spectra or TLC behaviour of these compounds. In all cases where we were able to establish the structures unequivocally however, the major isomer is the product of dihydroxylation syn to the dithiane 2-position substituent R as drawn. The structural assignment of the products in all other cases is based on the assumption that this pattern holds for all cases, and must therefore be regarded as tentative.
23. 15 Page, P. C. B; McKenzie, M. J.; Buckle, D. R. Tetrahedron, 1998, 54, 14573.