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DOI: 10.1055/s-0041-1738324
The Narasaka–Heck Cyclization
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Significance
Based on the finding that palladium(0) can cleave the N–O bond of sulfonyloximes, Tsutsui and Narasaka reported a catalytic protocol coupled with an intramolecular Heck-type cyclization to form pyrroles. Competing Beckmann rearrangement of the oxime derivatives could be suppressed by changing from the sulfonyl- to the pentafluorophenylacyl N-protecting group.
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Comment
In the following years, this method was successfully extended to access various N-heterocycles (see Review below). An enantioselective version for the synthesis of dihydropyrroles bearing a stereogenic center at the 2-position was introduced by Bower and co-workers (Chem. Sci. 2017, 8, 1981).
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Review
M. Kitamura, K. Narasaka Chem. Rec. 2002, 2, 268–277.
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Publication History
Article published online:
17 May 2022
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