Diastereospecific dihydroxylation and highly efficient asymmetric dihydroxylation kinetic resolution of cis/trans-2,6-dimethylbenzylidenecyclohexane

Chemical Communications

Volumn , Issue 24, 1996, Pages 2709-2710

  Gardiner, John M ^a   Nørret, Marck ^a   Sadler, Ian H ^b  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b UNIVERSITY OF EDINBURGH   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0344979435     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960002709     Document Type: Article

References (21)

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2. V. S. Martin, S. S. Woodward, T. Katsuki, Y. Yamada, M. Ikeda and K. B. Sharpless, J. Am. Chem. Soc., 1981, 103, 6237; R. A. Johnson and K. B. Sharpless, in Catalytic Asymmetric Synthesis, ed. 1. Ojima, VCH, New York, 1993, ch. 4.4.
3. (a) R. A. Johnson and K. B. Sharpless, in Catalytic Asymmetric Synthesis; ed. 1. Ojima, VCH, New York, 1993, ch. 4.1;
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6. J. M. Hawkins and A. Meyer, Science, 1993, 260, 1918; B. B. Lohray and V. Bhusan, Tetrahedron Lett., 1993, 34, 3911; F. J. A. D. Bakkeren, A. J. H. Klunder and B. Zwanberg, Tetrahedron, 1996, 52, 7901.
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8. While this study was ongoing, a kinetic resolution-recycling protocol appeared, employing high ligand (5-10%) and osmium (1-35%) loadings: C. W. Jefford and G. Timári, J. Chem. Soc., Chem. Commun., 1995, 1501.
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14. E. J. Corey, A. Guzman-Perez and M. C. Noe, J. Am. Chem. Soc., 1995, 117, 10805; P.-O. Norrby, H. Becker and K. B. Sharpless, J. Am. Chem. Soc., 1996, 118, 35, and references cited therein.
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18. rel Values calculated using the Kagan equation: H. B. Kagan and J. C. Fiaud, Top. Stereochem., 1988, 18, 249.
19. Steric effects blocking dihydroxylation syn to these diaxial methyls. This dihydroxylation is also consistent with the Cieplak model involving σ,σ* interactions: C. R. Johnson, B. D. Tait and A. S. Cieplak, J. Am. Chem. Soc., 1987, 109, 5875.
20. (Salen)-Mn catalysed epoxidation of the 1/ent-1 and 2/ent-2 mixture also leads to a single diastereoisomer derived from 2/ent-2, and kinetic resolution is observed: J. M. Gardiner, M. Nørret and I. H. Sadler, Tetrahedron Lett., 1996, in the press.
21. K. B. Sharpless, W. Amberg, Y. Bennani, G. A. Crispino, J. Hartung, K.-S. Jeong, H.-L. Kwong, K. Morikawa, Z.-M. Wang, D. Xu and X.-L. Zhang, J. Org. Chem., 1992, 57, 2768.