Asymmetric synthesis of (5S)-4-deoxy-5-C-(4-nitrophenyl)-L-threo-pentose and (5R)-5-C-(4-nitrophenyl)-L-arabinose

Article abstract of DOI:10.1016/S0040-4039(99)01832-8

In the presence of Eu(fod)₃, (1E)-(2',3',4',6'-tetra-O-acetyl-?2-D-glucopyranosyloxy)buta-1,3-diene and its (3Z)-4-O-acetyl derivative undergo Re-face and endo selective hereto Diels-Alder reactions with 4-nitrobenzaldehyde, 5-nitrofuran-2-carbaldehyde and 5-nitrothiophene-2-carbaldehyde. The cycloadducts are converted into the title compounds, early examples of 'free' 5-C-arylpentopyranoses.