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- W3159457638 abstract "• The C C bond cleavage reaction of α -oximino- β -ketoesters affords cyanoformates. • DAST is a pivotal dual-role reagent as a Lewis acid and fluoride ion donor. • High chemoselectivity observed in ketones over esters. A new protocol to synthesize cyanoformates was developed using simple β -ketoesters as substrates. (Diethylamino)sulfur trifluoride (DAST) was used as a dual-role reagent to activate the oxime moiety and to donate a fluoride. The key intermediates, α -oximino- β -ketoesters, were prepared by highly efficient acid-assisted oximation of β -ketoesters. Then, the deconstruction of α -oximino- β -ketoesters by the fluorinative C C bond cleavage was demonstrated to provide cyanoformates. In this event, the fluoride addition followed by the C C bond cleavage selectively occurred in the ketones over esters. Due to simple and mild reaction conditions, variously functionalized cyanoformates were exemplified." @default.
- W3159457638 created "2021-05-10" @default.
- W3159457638 creator A5042441205 @default.
- W3159457638 creator A5063903856 @default.
- W3159457638 date "2021-06-01" @default.
- W3159457638 modified "2023-09-27" @default.
- W3159457638 title "An expedient synthesis of cyanoformates via DAST-mediated C C bond cleavage of α-oximino-β-ketoesters" @default.
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- W3159457638 doi "https://doi.org/10.1016/j.tetlet.2021.153116" @default.
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