Journal
TETRAHEDRON-ASYMMETRY
Volume 21, Issue 2, Pages 208-215Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetasy.2009.12.017
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Funding
- CNRS
- University of Reims
- French Ministry of Education and Research
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The trimolecular condensation of indole, Meldrum's acid and chiral, sugar-derived aldehydes took place in good yield and high diastereoselectivity. The absolute configuration of the alpha-carbon of the chiral aldehydes ensured a predictable diastereocontrol of the newly created stereogenic centre except for (3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydrofuro[3,2-d][1,3]dioxole-5-carbaldehyde 3i. In this case, the opposite stereochemistry may be explained by a less congested conformer of the Knoevenagel-adduct intermediate. (C) 2010 Elsevier Ltd. All rights reserved.
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