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

M Helliwell, IM Phillips, RG Pritchard, RJ Stoodley

Index: Helliwell, Madeleine; Phillips, Iain M.; Pritchard, Robin G.; Stoodley, Richard J. Tetrahedron Letters, 1999 , vol. 40, # 49 p. 8651 - 8655

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Citation Number: 15

Abstract

In the presence of Eu (fod) 3,(1E)-(2′, 3′, 4′, 6′-tetra-O-acetyl-β-d-glucopyranosyloxy) buta-1, 3-diene and its (3Z)-4-O-acetyl derivative undergo Re-face and endo selective hetero 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.