Enantioselective [4 + 2] Cycloaddition of Cyclic N‑Sulfimines and Acyclic Enones or Ynones: A Concise Route to Sulfamidate-Fused 2,6-Disubstituted Piperidin-4-ones

Enantioselective [4 + 2] Cycloaddition of Cyclic N‑Sulfimines and Acyclic Enones or Ynones: A Concise Route to Sulfamidate-Fused 2,6-Disubstituted Piperidin-4-ones

A concise route to valuable sulfamate-fused 2,6-disubstituted piperidin-4-ones or 2,3-dihydropyridin-4(1H)-ones in good yield with high diastereo- and enantioselectivity is presented. The combination of chiral primary amine and o-fluorobenzoic acid efficiently promoted an asymmetric [4 + 2] cycloadd...

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Veröffentlicht in:Organic letters 2013-12, Vol.15 (23), p.6090-6093
Hauptverfasser: Liu, Yong, Kang, Tai-Ran, Liu, Quan-Zhong, Chen, Lian-Mei, Wang, Ya-Chuan, Liu, Jie, Xie, Yong-Mei, Yang, Jin-Liang, He, Long
Format: Artikel
Sprache:eng
Schlagworte:
Amines - chemistry
Catalysis
Cyclization
Cycloaddition Reaction
Imines - chemistry
Ketones - chemistry
Molecular Structure
Piperidones - chemical synthesis
Piperidones - chemistry
Stereoisomerism
Sulfones - chemical synthesis
Sulfones - chemistry
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Zusammenfassung:A concise route to valuable sulfamate-fused 2,6-disubstituted piperidin-4-ones or 2,3-dihydropyridin-4(1H)-ones in good yield with high diastereo- and enantioselectivity is presented. The combination of chiral primary amine and o-fluorobenzoic acid efficiently promoted an asymmetric [4 + 2] cycloaddition reaction of N-sulfonylimines and enones or ynones. The cycloaddition reaction between cyclic N-sulfonylimines and ynones is first reported.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol402977w