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- W2127318998 abstract "2-Bromoalka-1,n-dienes such as 9, 30 and 14 (n = 7) with tetrasubstituted methylenecyclopropane end groups, under palladium catalysis, underwent cyclization with cyclopropane-ring opening to give 2-ethenyl-3-methylene-1-cycloalkenes 41 (n = 6), 42 (n = 7), and 43, which are substituted monocyclic [3]dendralenes, in 65, 63 and 70 % yield, respectively. The same cross-conjugated trienes were isolated in good to excellent yields (77–92 %) from the corresponding 1,6- (10-H, 15) and 1,7-enynes (28-H) by a more atom-economic, palladium-catalyzed cycloisomerization. The vinylpalladium halide intermediate generated by initial carbopalladation of the 1,6-enyne 10-H with in situ generated phenylpalladium iodide also underwent the same cyclization cascade to yield the correspondingly phenyl-substituted cyclic [3]dendralene 41-Ph (21 %). The palladium-catalyzed cycloisomerization of the alk-1-ene-7,12-diyne 33-H gave the bicyclic cross-conjugated tetraene 50-H (43 %). Key features of the mechanism of the palladium-catalyzed cycloisomerization were proved using the specially designed model system 20-H. Like other cyclic [3]dendralenes, the ethenyl(methylene)cycloheptene 42 underwent a domino-Diels–Alder reaction with N-phenyltriazoline-3,5-dione to give a single diastereomer of the pentacyclic heterocycle 69 (77 % yield). (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)" @default.
- W2127318998 created "2016-06-24" @default.
- W2127318998 creator A5052144587 @default.
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- W2127318998 creator A5066795373 @default.
- W2127318998 creator A5081226022 @default.
- W2127318998 creator A5090577206 @default.
- W2127318998 date "2005-08-16" @default.
- W2127318998 modified "2023-10-10" @default.
- W2127318998 title "Intramolecular Heck Couplings and Cycloisomerizations of Bromodienes and Enynes with 1′,1′-Disubstituted Methylenecyclopropane Terminators: Efficient Syntheses of [3]Dendralenes" @default.
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- W2127318998 doi "https://doi.org/10.1002/ejoc.200500330" @default.
- W2127318998 hasPublicationYear "2005" @default.
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