Journal
TETRAHEDRON
Volume 65, Issue 17, Pages 3502-3508Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.02.020
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Funding
- Consejo Nacional de Investigaciones Cientificas y Tecnicas (CONICET)
- Agencia Nacional de Promocion Cientifica y Tecnologica (ANPCyT)
- The International Foundation for Science (IFS)
- Organization for the Prohibition of Chemical Weapons (OPCW)
- The Netherlands
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Chiral alcohols were designed and easily prepared from levoglucosenone, a biomass-derived valuable synthon. These alcohols were tested as chiral auxiliaries in asymmetric Diels-Alder reactions between the corresponding acrylates with acyclic and cyclic dienes. The regio, stereo, and facial selectivity varied from very good to excellent, depending upon the benzylic substitution of the auxiliary and the diene employed. As a consequence, after removal of the auxiliary, the resulting carboxylic acid derivatives were obtained in 72-99% ee. (C) 2009 Elsevier Ltd. All rights reserved.
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