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Rhodium-Catalyzed Asymmetric Aqueous Pauson–Khand-Type Reaction
✍ Scribed by Fuk Yee Kwong; Yue Ming Li; Wai Har Lam; Liqin Qiu; Hang Wai Lee; Chi Hung Yeung; Kin Shing Chan; Albert S. C. Chan
- Publisher
- John Wiley and Sons
- Year
- 2005
- Tongue
- English
- Weight
- 295 KB
- Volume
- 11
- Category
- Article
- ISSN
- 0947-6539
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✦ Synopsis
Abstract
An interesting rhodium‐catalyzed asymmetric aqueous Pauson–Khand‐type reaction was developed. A chiral atropisomeric dipyridyldiphosphane ligand was found to be highly effective in this system. This operationally simple protocol allows both catalyst and reactants to be handled under air without precautions. Various enynes were transformed to the corresponding bicyclic cyclopentenones in good yield and enantiomeric excess (up to 95 % ee). A study of the electronic effects of the enyne substrates revealed a correlation between the electronic properties of the substrates and the ee value obtained in the product of the Pauson–Khand‐type reaction. A linear free‐energy relationship was observed from a Hammett study.
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