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Volumn 119, Issue 8, 1997, Pages 1840-1858

Toward an understanding of the high enantioselectivity in the osmium-catalyzed asymmetric dihydroxylation. 4. Electronic effects in amine-accelerated osmylations

Author keywords

[No Author keywords available]

Indexed keywords

OSMIUM; STYRENE DERIVATIVE;

EID: 0030966686     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961464t     Document Type: Article
Times cited : (125)

References (130)
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    • For examples of models based on the "[3 + 2]" pathway, see: (a) Corey, E. J.; Noe, M. C. J. Am. Chem. Soc. 1993, 115, 12579. (b) Corey, E. J.; Noe, M. C.; Sarshar, S. Tetrahedron Lett. 1994, 35, 2861. (c) Corey, E. J.; Noe, M. C.; Grogan, M. J. Tetrahedron Lett. 1994, 35, 6427. (d) Corey, E. J.; Guzman-Perez, A.; Noe, M. C. J. Am. Chem. Soc. 1994, 116, 12109. (e) Corey, E. J.; Guzman-Perez, A.; Noe, M. C. J. Am. Chem. Soc. 1995, 117, 10805. (f) Corey, E. J.; Noe, M. C.; Guzman-Perez. A. J. Am. Chem. Soc. 1995, 117, 10817.
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    • Derivations of the rate expressions corresponding to the different mechanisms are included in the Supporting Information.
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    • note
    • The observation of Michaelis-Menten-like kinetic behavior in the catalytic AD reported by Corey and Noe (ref 73) results from a step other than osmylation. Kinetic studies on the stoichiometric AD of styrene under conditions that replicate the organic phase of the catalytic AD reveal that the rate expression is clearly first order in styrene over a wide range of concentrations. Nelson, D. W.; Sharpless, K. B. Unpublished results.
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    • See ref 10b and references cited therein for the latest refinements in this model
    • See ref 10b and references cited therein for the latest refinements in this model.


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