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- W4243713042 endingPage "14473" @default.
- W4243713042 startingPage "14469" @default.
- W4243713042 abstract "Carbonyl-substituted allenes are highly important synthetic intermediates for a number of heterocycles and strained-ring systems. However, chemistry of allenyl aldehydes has not been explored as extensively as their ketone, ester, or amide analogues because of a lack of general synthetic methods. Described herein is the first direct α-vinylidenation of aldehydes and an α-vinylidenation/γ-functionalization cascade to access tri- and tetrasubstituted allenyl aldehydes using a combination of a gold catalyst and an secondary amine. The reactive enamine intermediate of an aldehyde reacts with the gold-activated hypervalent silylethynyl benziodoxolone to selectively generate the corresponding trisubstituted allenyl aldehyde. The allenyl aldehyde can further react with another equivalent of the alkynylation reagent or other electrophiles to afford tetrasubstituted allenes bearing an aldehyde group, an acetylene, and a halogen functionality. This method enables rapid access to polysubstituted furans from aldehydes." @default.
- W4243713042 created "2022-05-12" @default.
- W4243713042 creator A5065502904 @default.
- W4243713042 creator A5065924240 @default.
- W4243713042 creator A5089382124 @default.
- W4243713042 date "2013-11-28" @default.
- W4243713042 modified "2023-09-26" @default.
- W4243713042 title "Direct α-Vinylidenation of Aldehydes and Subsequent Cascade: Gold and Amine Catalysts Work Synergistically" @default.
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- W4243713042 doi "https://doi.org/10.1002/ange.201308835" @default.
- W4243713042 hasPublicationYear "2013" @default.
- W4243713042 type Work @default.
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