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

Authors
Helliwell, M Phillips, IM Pritchard, RG Stoodley, RJ
Citation
M. Helliwell et al., Asymmetric synthesis of (5S)-4-deoxy-5-C-(4-nitrophenyl)-L-threo-pentose and (5R)-5-C-(4-nitrophenyl)-L-arabinose, TETRAHEDR L, 40(49), 1999, pp. 8651-8655
Citations number
19
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
49
Year of publication
1999
Pages
8651 - 8655
Database
ISI
SICI code
0040-4039(199912)40:49<8651:ASO(A>2.0.ZU;2-5
Abstract
In the presence of Eu(fod)(3), (1E)-(2',3',4',6'-tetra-O-acetyl-beta-D-gluc opyranosyloxy)buta-1,3-diene and its (3Z)-4-O-acetyl derivative undergo Re- face and endo selective hetero Diels-Alder reactions with 4-nitrobenzaldehy de, 5-nitrofuran-2-carbaldehyde and 5-nitrothiophene-2-carbaldehyde. The cy cloadducts are converted into the title compounds, early examples of 'free' 5-C-arylpentopyranoses. (C) 1999 Published by Elsevier Science Ltd. All ri ghts reserved.