2024
DOI: 10.1002/adsc.202400261
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Desymmetrization of Cyclohexadienones via [3+2]/[2+1] Domino Annulation: Access to Cyclopropane Fused Tricyclic Enones

Yannan Zhu,
Sen Wang,
Bo Fang
et al.

Abstract: A [3+2]/[2+1] domino annulation reaction of cyclohexadienones and α‐aryl vinylsulfonium salts has been reported. A range of cyclopropane fused tricyclic enones bearing four contiguous stereocenters were obtained as a single diastereomer in 44‐93% yields. The synthetic utility was demonstrated with the gram‐scale reactions and further transformations of the products.

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(2 citation statements)
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“…We would like to add a new reference (would be ref 10 in our original work but labeled as ref below) citing the published work of Zhu et al Adv. Synth.…”
mentioning
confidence: 92%
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“…We would like to add a new reference (would be ref 10 in our original work but labeled as ref below) citing the published work of Zhu et al Adv. Synth.…”
mentioning
confidence: 92%
“…In conclusion, we have disclosed a straightforward approach to construct hydroindoline-5-one-based 6/5/3-fused polycyclic ring structures through multistep cascade reactions of para -quinamines and α-aryl vinylsulfoniums tetraphenylborate. In the presence of mild conditions, the reactions proceed smoothly to deliver the desired products in generally good yields . This protocol is also applicable to para -quinols to furnish hydrobenzofuran-5-one-based 6/5/3-tricyclic scaffolds.…”
mentioning
confidence: 99%