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Claisen rearrangements of lactonic (silyl) enolates: a new route to functionalized cycloalkenes

โœ Scribed by Danishefsky, Samuel; Funk, Raymond L.; Kerwin, James F.


Book ID
126312453
Publisher
American Chemical Society
Year
1980
Tongue
English
Weight
388 KB
Volume
102
Category
Article
ISSN
0002-7863

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## Abstract Allenic silyl ketene acetals 3 formed by conjugate 1,6โ€addition of organocuprates to 2โ€propenโ€1โ€yl and 2โ€butenโ€1โ€yl 2โ€enโ€4โ€ynoates 1 and regioselective enolate capture with silyl electrophiles readily undergo [3,3]โ€Irelandโ€Claisen rearrangements to the 2โ€substituted methyl 3,4โ€dienoates

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Allylic oxygen to carbon bond transposition on graphite oxide (additional substrate oxygen groups have been removed for clarity).