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Synthesis 1987; 1987(10): 900-904
DOI: 10.1055/s-1987-28114
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Reactivity and Diastereoselectivity in Inverse- Type Hetero-Diels-Alder Dihydropyran Syntheses

Satyam Apparao* , Martin E. Maier, Richard R. Schmidt
  • *Fakultät Chemie, Universität Konstanz, Postfach 5500, D-7750 Konstanz, West Germany
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Publication Date:
12 September 2002 (online)

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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.