Search results for "L-ERYTHRULOSE"
showing 3 items of 3 documents
Diastereoselective synthesis of enantiomeric tertiary alcohols via nucleophilic additions to protected D- and L-erythrulose derivatives
1992
Abstract The diastereoselectivity of the addition of several organometallic reagents to the carbonyl group of protected D - and L -erythrulose derivatives has been investigated. Tertiary alcohols are stereoselectively formed, the diastereomeric ratio being markedly dependent on the reagent type, solvent and temperature.
Double diastereoselection in aldol reactions mediated by dicyclohexylchloroborane between L-erythrulose derivatives and chiral aldehydes. The Felkin-…
2003
Both matched and mismatched diastereoselections have been observed in aldol reactions of the B,B-dicyclohexylboron enolate of a protected l-erythrulose derivative with a range of chiral aldehydes. The stereochemical outcome of reactions with alpha-methyl aldehydes can be adequately explained within the Felkin-Anh paradigm. In the case of alpha-oxygenated aldehydes, however, strict adherence to this model does not allow for a satisfactory account of the observed results. In such cases, the Cornforth model provides a much better explanation.
Highly diastereoselective additions of organometallic reagents to 1-O-silylated 3,4-Di-O-benzyl-L-erythrulose derivatives
1993
Abstract The diastereoselectivity of the addition of several organometallic reagents to the carbonyl group of the title compounds has been investigated. Some organomagnesium reagents display high diastereoselectivities (90–99%) and the major products are those predicted by the α-chelation model.