1998
DOI: 10.1021/cr970029u
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Synthesis of Functionalized Bicyclo[3.2.1]octanes and Their Multiple Uses in Organic Chemistry

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Cited by 184 publications
(80 citation statements)
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References 431 publications
(569 reference statements)
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“…Reagents and conditions: (a) LDA, THF, -78ºC then CNCO 2 It is interesting to note that the intramolecular Diels-Alder reaction of the 5-vinyl-1,3-cyclohexadiene moiety is strongly preferred to other alternative intramolecular cycloadditions that were also attempted, in spite of the highly strained transition state presumably involved. Thus, when compound 13 (and also the corresponding dimethyl(vinyl)silyl analogue, 13 with R 2 = OSiMe 2 CH=CH 2 ), readily prepared from hydroxycarvone 10 as described in the Experimental section, was heated in toluene under the same conditions described above for 7, only the Diels-Alder adduct 14 was formed, without any appreciable amounts of the adduct resulting from the alternative intramolecular cycloaddition of the 1,3,10-undecatriene moiety being observed [12].…”
Section: Methodsmentioning
confidence: 99%
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“…Reagents and conditions: (a) LDA, THF, -78ºC then CNCO 2 It is interesting to note that the intramolecular Diels-Alder reaction of the 5-vinyl-1,3-cyclohexadiene moiety is strongly preferred to other alternative intramolecular cycloadditions that were also attempted, in spite of the highly strained transition state presumably involved. Thus, when compound 13 (and also the corresponding dimethyl(vinyl)silyl analogue, 13 with R 2 = OSiMe 2 CH=CH 2 ), readily prepared from hydroxycarvone 10 as described in the Experimental section, was heated in toluene under the same conditions described above for 7, only the Diels-Alder adduct 14 was formed, without any appreciable amounts of the adduct resulting from the alternative intramolecular cycloaddition of the 1,3,10-undecatriene moiety being observed [12].…”
Section: Methodsmentioning
confidence: 99%
“…With the tricyclic system 15 at hand, we investigated the opening of the cyclopropane ring in order to elaborate the bicyclo[3.2.1]octane framework. In the literature, dissolving metal reductions with metal-ammonia systems has been the most frequently used method for the cleavage of cyclopropyl ketones [2]. The electron transfer homogenous reagent samarium(II) iodide has been less often used for this purpose, although some examples of samarium(II)-mediated cyclopropane cleavage of rigid cyclopropyl ketones have been described [2,13].…”
Section: Methodsmentioning
confidence: 99%
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