C. Andrés, Alfonso González, R. Pedrosa
Aug 11, 1992
Citations
0
Influential Citations
20
Citations
Journal
Tetrahedron Letters
Abstract
Abstract Condensation of (R)-N-benzyl-2-phenylglycinol 1 with the methyl hemiacetal of ethyl glyoxylate leads to (2S,4R)-2-ethoxycarbonyl-4-phenyl-1,3-oxazolidine 2 as the major product, obtained as a pure enantiomer after column chromatography. Compound 2 is stereoselectively cleaved by dialkylzinc reagents, prepared from alkylmagnesium iodides and ZnCl 2 , with moderate to good d.e.ś (72–94 %). These compounds, after separation by column chromatography and debenzylation by hydrogenolysis in the presence of 10% Pd on carbon, lead to enantiomerically pure ethyl α-amino carboxylates with good chemical yields.