1998
DOI: 10.1016/s0957-4166(97)00627-7
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Enantioselective synthesis of 1-nitrotricyclo[5,2,2,02,6]undeca-3,8-dienes via tandem consecutive asymmetric Diels–Alder reaction–Cope rearrangement

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Cited by 11 publications
(3 citation statements)
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“…The former was completely stable at room temperature, but could be quantitatively transformed to the latter by heating at 130 °C, thereby demonstrating the partial involvment of the [3,3] sigmatropic rearrangement in the process. An analogous case was more recently reported for the reaction between cyclopentadiene 4b and 6-substituted 1-nitrocyclohexadienes …”
Section: Discussionsupporting
confidence: 69%
“…The former was completely stable at room temperature, but could be quantitatively transformed to the latter by heating at 130 °C, thereby demonstrating the partial involvment of the [3,3] sigmatropic rearrangement in the process. An analogous case was more recently reported for the reaction between cyclopentadiene 4b and 6-substituted 1-nitrocyclohexadienes …”
Section: Discussionsupporting
confidence: 69%
“…Thus, starting from 266 , the major product (70% yield) was 1-nitrotricyclo[5.2.2.0 2,6 ]undecadiene 270 , which is actually the consequence of a sigmatropic Cope rearrangement of the initially formed endo -norbornenic cycloadduct 269 . Also, a very small quantity of 269 and its exo -isomer 268 were isolated by preparative thin-layer chromatography from the reaction mixture (Scheme ) …”
Section: -Nitro-13-dienesmentioning
confidence: 99%
“…A tandem reaction of an initial Diels-Alder cycloaddition and a consecutive Cope rearrangement was published by Serrano. 78…”
Section: Scheme 68mentioning
confidence: 99%