95299-24-4Relevant articles and documents
Enantioselective deprotonation of 2,6-disubstituted cyclohexanones with a homochiral magnesium amide base and the observation of a novel kinetic resolution process
Henderson,Kerr,Moir
, p. 1253 - 1256 (2001)
A recently developed homochiral magnesium amide base has been shown to be highly effective in the asymmetric deprotonation of cis-2,6-disubstituted cyclohexanones, affording excellent levels of both conversion and enantioselection (up to >99.5:0.5 e.r.).
Magnesium amide base-mediated enantioselective deprotonation processes
Henderson, Kenneth W,Kerr, William J,Moir, Jennifer H
, p. 4573 - 4587 (2007/10/03)
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.
