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37049092382
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note
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This versatile building block has been constructed by the Diels-Alder reaction of 1,1-dimethoxy-3-siloxy-1,3-butadiene or its derivatives with alkenes. The Diels-Alder reaction of such dienes with alkyne or quinone was also a very powerful method for synthesizing resorcinols. However, they require several steps for preparation. For preparation, see
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For various conversions of the Diels-Alder adduct derived from the diene
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34
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77952992684
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note
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The isomerized product 18 was obtained in 22% yield (containing trace inseparable compound) at this step. So far, we do not have any information about the mechanism of this isomerization. Further screenings of the conditions to selectively give 18 and a mechanistic study are in progress.
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35
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37
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77953004744
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note
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We have previously determined the absolute configuration of Diels-Alder adducts of our asymmetric reaction using (S)-BINAMIDE by conversion to a known compound. (3a) For details, see the Supporting Information.
-
-
-
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38
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77952970845
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note
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The absolute configuration of synthetic (+)-platyphyllide was also estimated by Moshers method. For details, see the Supporting Information.
-
-
-
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39
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77953007044
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note
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CCDC 773055 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
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