27088-69-3Relevant articles and documents
A broadly applicable and practical oligomeric (salen)Co catalyst for enantioselective epoxide ring-opening reactions
White, David E.,Tadross, Pamela M.,Lu, Zhe,Jacobsen, Eric N.
supporting information, p. 4165 - 4180 (2014/06/09)
The (salen)Co catalyst (4a) can be prepared as a mixture of cyclic oligomers in a short, chromatography-free synthesis from inexpensive, commercially available precursors. This catalyst displays remarkable enhancements in reactivity and enantioselectivity relative to monomeric and other multimeric (salen)Co catalysts in a wide variety of enantioselective epoxide ring-opening reactions. The application of catalyst 4a is illustrated in the kinetic resolution of terminal epoxides by nucleophilic ring-opening with water, phenols, and primary alcohols; the desymmetrization of meso epoxides by addition of water and carbamates; and the desymmetrization of oxetanes by intramolecular ring opening with alcohols and phenols. The favorable solubility properties of complex 4a under the catalytic conditions facilitated mechanistic studies, allowing elucidation of the basis for the beneficial effect of oligomerization. Finally, a catalyst selection guide is provided to delineate the specific advantages of oligomeric catalyst 4a relative to (salen)Co monomer 1 for each reaction class.
Oxidative Displacement of Hypervalent Iodine from Alkyl Iodides
Cambie, Richard C.,Chambers, David,Lindsay, Barry G.,Rutledge, Peter S.,Woodgate, Paul D.
, p. 822 - 827 (2007/10/02)
Oxidative displacement of iodine from primary alkyl iodides and vic-substituted iodocyclohexanes with m-chloroperbenzoic acid in either dichloromethane or t-butyl alcohol-water gives primary alcohols and vic-substituted cyclohexanols, respectively.Retention of configuration at the displacement centre occurs for all of the trans-vic-substituted iodocyclohexanes except the iodoacetate and iodotrifluoroacetate where inversion of configuration occurs to give cis-hydroxy-esters.Oxidation of (S)-2-iodo-octane occurs with almost complete inversion to give (R)-octan-2-ol but also affords octan-1-ol, octan-3-ol, and octan-2-one.
