Journal
PURE AND APPLIED CHEMISTRY
Volume 80, Issue 5, Pages 1135-1140Publisher
INT UNION PURE APPLIED CHEMISTRY
DOI: 10.1351/pac200880051135
Keywords
cycloaddition; nitrones; palladium catalyst; asymmetric catalysis
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A new type of reagent, gamma-methylidene-delta-valerolactones, has been devised, which acts as a four-carbon unit in a Pd-catalyzed cycloaddition reaction through the formation of a 1,4-zwitterionic species. The utility has been demonstrated in the context of stereoselective [4+3] cycloaddition with nitrones to provide highly functionalized 1,2-oxazepines, including the asymmetric variant with high enantioselectivity.
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