Divergent reaction pathways of a cationic intermediate: rearrangement and cyclization of 2-substituted furyl and benzofuryl enones catalyzed by iridium(III).

doi:10.1021/ja111317q

Paper

Divergent reaction pathways of a cationic intermediate: rearrangement and cyclization of 2-substituted furyl and benzofuryl enones catalyzed by iridium(III).

Published Feb 15, 2011 · Tulaza Vaidya, Gerald F. Manbeck, Sylvia Chen

Journal of the American Chemical Society

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Abstract

In contrast to 2-substituted pyrrole enones, furyl and benzofuryl enones do not undergo the Nazarov electrocyclization. Instead, these furyl and benzofuryl enones exhibit unusual rearrangement sequences in the presence of catalytic amounts of [IrBr(CO)(DIM)((R)-(+)-BINAP)](SbF(6))(2) (1; DIM = diethylisopropylidene malonate) and AgSbF(6) (1:1). A 1,2-H shift followed by intramolecular Friedel-Crafts alkylation leads to synthetically valuable cyclohexanones with furanylic quaternary centers. The electrophilicity of 1 is essential for this rearrangement.

Study Snapshot

This study demonstrates that iridium(III) catalyzes the rearrangement and cyclization of 2-substituted furyl and benzofuryl enones, leading to synthetically valuable cyclohexanones with furanylic quaternary centers.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Divergent reaction pathways of a cationic intermediate: rearrangement and cyclization of 2-substituted furyl and benzofuryl enones catalyzed by iridium(III).

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References

Citations

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