An Atropisomerically Enforced Phosphoric Acid for Organocatalytic Asymmetric Reactions
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- Luca Bernardi
- Department of Industrial Chemistry “Toso Montanari” University of Bologna Viale Risorgimento 4 40136 Bologna Italy
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- Giada Bolzoni
- Department of Industrial Chemistry “Toso Montanari” University of Bologna Viale Risorgimento 4 40136 Bologna Italy
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- Mariafrancesca Fochi
- Department of Industrial Chemistry “Toso Montanari” University of Bologna Viale Risorgimento 4 40136 Bologna Italy
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- Michele Mancinelli
- Department of Industrial Chemistry “Toso Montanari” University of Bologna Viale Risorgimento 4 40136 Bologna Italy
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- Andrea Mazzanti
- Department of Industrial Chemistry “Toso Montanari” University of Bologna Viale Risorgimento 4 40136 Bologna Italy
書誌事項
- 公開日
- 2016-05-02
- 権利情報
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- http://onlinelibrary.wiley.com/termsAndConditions#vor
- DOI
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- 10.1002/ejoc.201600296
- 公開者
- Wiley
この論文をさがす
説明
<jats:p>Three BINOL‐derived phosphoric acids exhibiting atropisomerism in the 3,3′‐positions were obtained by Suzuki coupling reaction. The diastereomeric mixture was resolved by HPLC. Structural assignment was achieved by NOE‐NMR analysis and by TD‐DFT simulation of the electronic circular dichroism (ECD) spectra. The three atropisomeric catalysts were tested in three enantioselective reactions, comparing their ability to induce enantioselectivity with related, well‐known, phosphoric acid structures. All three catalysts were competent in promoting the reactions, rendering excellent enantioselectivity (98 % <jats:italic>ee</jats:italic>) in one case. The atropisomeric features at the 3,3′‐position were indeed found to influence the outcome of the reaction, demonstrating the potential of atropisomeric conformational control at the 3,3′‐position of the BINOL core in the rationalization of catalyst performances and in the design of new efficient structures.</jats:p>
収録刊行物
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- European Journal of Organic Chemistry
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European Journal of Organic Chemistry 2016 (19), 3208-3216, 2016-05-02
Wiley