Reactivity and Diastereoselectivity in Inverse- Type Hetero-Diels-Alder Dihydropyran Syntheses
- 1 January 1987
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1987 (10) , 900-904
- https://doi.org/10.1055/s-1987-28114
Abstract
β-Acyloxy-α-phenylthio-substituted α,β-unsaturated carbonyl compounds 3a-i and 4c, f, having different electron withdrawing carbon substituents at the carbonyl group, afford with ethyl vinyl ether as heterodienophile the dihydropyrans 5a-i and 6c, f, respectively. The endo/exo-diastereoselectivity of these reactions, providing versatile intermediates for carbohydrate and related natural product syntheses, is discussed.Keywords
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