Kerr, W.J. and Henderson, K.W. and Moir, J.H. (2002) Magnesium amide base-mediated enantioselective deprotonation processes. Tetrahedron, 58 (23). pp. 4573-4587. ISSN 0040-4020Full text not available in this repository. (Request a copy from the Strathclyde author)
A novel homochiral magnesium bisamide has been readily prepared and, following careful optimisation, this species has been shown to react efficiently with a series of prochiral 4-substituted cyclohexanones in the presence of TMSCl to give the corresponding silyl enol ethers in enantiomeric ratios of up to 95:5. Additionally, the same chiral base system has been shown to be highly effective in the desymmetrisation of cis-2,6-disubstituted cyclohexanones, providing excellent levels of both conversion and enantioselection (up to >99.5:0.5 er). Furthermore, the magnesium bisamide has also been shown to mediate a kinetic resolution process with the corresponding trans-disubstituted substrates, allowing access to enantioenriched enol ethers and ketones.
|Keywords:||deprotonation processes , enantioselective deprotonation processes , magnesium amides, Chemistry, Biochemistry, Organic Chemistry, Drug Discovery|
|Subjects:||Science > Chemistry|
|Department:||Faculty of Science > Pure and Applied Chemistry
|Depositing user:||Pure Administrator|
|Date Deposited:||12 Mar 2012 15:21|
|Last modified:||22 Mar 2017 09:57|