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Synfacts 2022; 18(06): 0651
DOI: 10.1055/s-0041-1738324
Metals in Synthesis

The Narasaka–Heck Cyclization

Contributor(s):
Martin Oestreich
,
Hendrik F. T. Klare
,
Benedikt Wolff
Tsutsui H, Narasaka K. * The University of Tokyo, Japan
Synthesis of Pyrrole Derivatives by the Heck-Type Cyclization of γ,δ-Unsaturated Ketone O-Pentafluorobenzoyloximes.

Chem. Lett. 1999;
28: 45-46
DOI: 10.1246/cl.1999.45.
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Key words

amino-Heck cyclization - oximes - palladium catalysis - pyrroles

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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