A new methodology of intramolecular hetero Diels-Alder reaction with β-alkoxy-substituted conjugated nitroalkenes as heterodienes: stereoselective one-pot synthesis of trans-fused bicyclic γ-lactones |
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| Authors: | Eiji Wada Masahiko Yoshinaga |
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| Institution: | a Institute for Materials Chemistry and Engineering, Kyushu University, 6-1 Kasugakoen, Kasuga 816-8580, Japan
b Department of Molecular and Material Science, Graduate School of Engineering Sciences, Kyushu University, 6-1 Kasugakoen, Kasuga 816-8580, Japan |
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| Abstract: | Tandem reaction of (E)-1-ethoxy-2-nitroethylene with δ,ε-unsaturated alcohols leading to stereoselective trans-fused bicyclic γ-lactones has been developed using a catalytic amount of a Lewis acid such as Yb(OTf)3 and Ni(ClO4)2·6H2O. This process involves the stereoselective tandem transetherification-intramolecular hetero Diels-Alder reaction leading to bicyclic nitronates, and sequential transformation of the nitronate moiety to a lactone functional group under similar reaction conditions in good yields. |
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| Keywords: | nitroalkene intramolecular hetero Diels-Alder reaction Lewis acid tandem reaction transetherification δ ε-unsaturated alcohols molecular sieves |
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