57456-95-8Relevant academic research and scientific papers
Stereo- and regioselectivity in the P450-catalyzed oxidative tandem difunctionalization of 1-methylcyclohexene
Roiban, Gheorghe-Doru,Agudo, Rubén,Reetz, Manfred T.
, p. 5306 - 5311 (2013/07/05)
The selective partial oxidation of small non-functionalized molecules using biocatalysis based on P450 monooxygenases is known to be difficult due to the expected poor regio- and stereoselectivity, but in this study it was nevertheless attempted. 1-Methyl
Diastereoselective epoxidation of allylically substituted alkenes using metalloporphyrin catalysts
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Page/Page column 4, (2008/06/13)
Diastereoselective epoxidation of allylically substituted alkenes using metalloporphyrins as catalyst provides high trans-selectivities (i.e., trans-:cis-epoxide ratio). A diversity of cycloalkenes bearing different allylic substituents are shown to be efficiently epoxidized to afford the corresponding trans-epoxides with excellent trans-selectivities (up to >98%) and good yields (up to 99%). Acyclic allylic alkenes bearing different allylic substituents are efficiently epoxidized to afford the corresponding erythro-epoxides with good erythro-selectivities. The metalloporphyrin-catalyzed reactions exhibit up to 20 times higher trans-selectivities than the conventional method using m-chloroperoxybenzoic acid as oxidant.
Diastereoselectivity in the epoxidation of substituted cyclohexenes by dimethyldioxirane
Murray, Robert W.,Singh, Megh,Williams, Brian L.,Moncrieff, Hazel M.
, p. 1830 - 1841 (2007/10/03)
Three series of compounds based on the cyclohexene framework have been epoxidized by dimetbyldioxirane. A pronounced dependence of epoxide diastereoselectivity on substituent has been observed. In addition there is a solvent influence on this stereoselectivity. The results have been explained by invoking steric, H-bonding, and dipole - dipole influences on the epoxide stereochemistry.
