Matthew J. Palmer

Novel catalysts for asymmetric reduction of carbonyl groups

The use of (i) enantiomerically pure phosphinamides coupled to borane and (ii) an enantiomerically pure amino alcohol coupled to a transfer hydrogenation process, in the asymmetric catalysis of the reduction of ketones to alcohols, is described. The former process is particularly suited to the reduction of alpha-chlorinated substrates, affording e.e.s of up to 94%, whilst the latter process is optimal for unfunctionalised ketones, affording e.e.s of up to 98%.

Recent developments in the area of asymmetric transfer hydrogenation

The use of an enantiomerically pure amino alcohol, coupled to a transfer hydrogenation process, in the asymmetric catalysis of the reduction of ketones to alcohols, is described. The process works well for unfunctionalised ketones, affording e.e.s of up to 98%, and excellent conversions. We have recently extended, for the first time in this application, the scope of the methodology to the reductions of a-heteroatom substituted substrates, through the use of the appropriate protecting groups on each atom.

The use of phosphinamide N-protecting groups in the diastereoselective reduction of ketones

Abstract The phosphinamide N-protecting group is demonstrated to be an effective directing group for diastereoselective reductions of proximal ketones. A range of methods for the preparation of the requisite α-amino ketones substrates are described.

Asymmetric transfer hydrogenation of ketones using amino alcohol and monotosylated diamine derivatives of indane

A series of 1,2-amino alcohol and 1,2-monotosylated diamine derivatives of indane have been applied as ligands in the asymmetric ruthenium(II)-catalysed transfer hydrogenation reaction of a series of ketones. Of these, the cis-1-aminoindan-2-ol derivative gives some of the highest asymmetric inductions reported for any amino alcohol ligand in this application.