Journal
TETRAHEDRON
Volume 65, Issue 28, Pages 5571-5576Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.01.112
Keywords
Asymmetric synthesis; Chan's diene; Organocatalysis; Hydrogen bonding; Vinylogous aldol reaction; Hetero-Diels-Alder reaction
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Funding
- Universita di Salerno
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Chan's diene proved to react with aromatic aldehydes under organocatalytic conditions in presence of a chiral naphthyl-TADDOL derivative to give vinylogous aldols (up to 65% ee) with complete gamma-selectivity. A further process of hetero-Diels-Alder cycloaddition, leading to chiral pyran-4-one derivatives (up to 60% ee), was favoured by electron-withdrawing substituents on the aromatic ring. (C) 2009 Elsevier Ltd. All rights reserved.
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