期刊
TETRAHEDRON
卷 61, 期 24, 页码 5822-5830出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.04.016
关键词
asymmetric catalysis; dihydropyrone; Hetero-Diels-Alder reaction; titanium (IV) complex
An efficient enantioselective approach to 2,5-disubstituted dihydropyrones was developed. Some easily accessible inexpensive diol ligand metal complexes were employed, and [(R)-BINOL](2)-Ti(OiPr)4 complex was found to be the most effective catalyst (up to 99% yield and 99% ee in the presence of 5 mol% catalyst) for the hetero-Diels-Alder reaction between trans-1-methoxy-2-methyl-3-trimethylsiloxybuta-1,3-diene (1) and aldehydes. The potential and generality of this catalyst were evaluated by a variety of aldehydes including aromatic, heteroaromatic, alpha,beta-unsaturated and aliphatic aldehydes. Based on the isolated intermediate from the reaction of benzaldehyde being confirmed by H-1, C-13 NMR and FIRMS data, the mechanism was proposed as a Mukaiyama addol pathway. (c) 2005 Elsevier Ltd. All rights reserved.
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