133756-20-4Relevant academic research and scientific papers
Asymmetric synthesis by the use of norephedrine-derived 2-methoxy-oxazolidines. Part four: the synthesis of enantiomerically enriched polyhydroxylated building blocks
Bernardi, A.,Piarulli, U.,Poli, G.,Scolastico, C.,Villa, R.
, p. 751 - 757 (2007/10/02)
The Lewis acid promoted addition of five silylketeneacetals to norephedrine derived 2-methoxy oxazolidines allowed the stereoselective incorporation of an oxy function vicinal to the oxazolidinic C-2 position.Subsequent functional group modification and/or non destructive chirophor removal, afforded enantiomerically enriched polyhydroxylated building blocks such as (S)-di-O-benzyl glyceraldehyde and D-ribose propane-1,3 diyldithioacetal.A rational accounting for the selectivity of the coupling steps is proposed.Keywords: asymmetric synthesis / norephedrine / (S)-di-O-benzylglyceraldehyde / D-ribose propane-1,3-diyldithioacetal
