Journal
JOURNAL OF ORGANOMETALLIC CHEMISTRY
Volume 691, Issue 10, Pages 2182-2198Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jorganchem.2005.11.009
Keywords
osmium; asymmetric synthesis; dihydroxylation; molecular modeling; kinetics
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The interactions between the substrate and the ligand in the Sharpless AD reaction have been examined in detail, using a combination of substrate competition experiments and molecular modeling of transition states. There is a good agreement between computational and experimental results, in particular for the stereo selectivity of the reaction. The influence of each moiety in the second-generation ligand (DHQD)(2)PHAL on the rate and selectivity of the reaction has been elucidated in detail. (c) 2005 Elsevier B.V. All rights reserved.
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