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I2-Promoted formal [3+2] cycloaddition of α-methylenyl isocyanides with methyl ketones: a route to 2,5-disubstituted oxazoles.

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An I2-promoted formal [3+2] cycloaddition for access to oxazoles has been demonstrated. This is the first example of a Lewis acid-promoted formal [3+2] cycloaddition of isocyanides with methyl ketones involving… Click to show full abstract

An I2-promoted formal [3+2] cycloaddition for access to oxazoles has been demonstrated. This is the first example of a Lewis acid-promoted formal [3+2] cycloaddition of isocyanides with methyl ketones involving the C[triple bond, length as m-dash]N cleavage of isocyanides. The salient feature of this approach is unconventional 2,5-disubstituted oxazole formation from isocyanides and ketones rather than 4,5-substituted oxazoline.

Keywords: methyl ketones; cycloaddition methylenyl; promoted formal; formal cycloaddition; isocyanides methyl

Journal Title: Chemical communications
Year Published: 2017

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