Title:
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Immobilization of cis-4-Hydroxydiphenylprolinol Silyl Ethers onto Polystyrene. Application in the Catalytic Enantioselective Synthesis of 5-Hydroxyisoxazolidines in Batch and Flow
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Author:
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Lai, Junshan; Sayalero, Sonia; Ferrali, Alessandro; Osorio-Planes, Laura; Bravo, Fernando; Rodríguez-Escrich, Carles; Pericàs, Miquel A.
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Abstract:
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A new family of polystyrene-supported cis-4-hydroxydiphenylprolinol silyl ethers has been prepared, and the resulting polymers have been evaluated as organocatalysts to promote the tandem reaction between N-protected hydroxylamines and α,β-unsaturated aldehydes in batch and flow. The new PS-supported catalysts compare favorably with well-established immobilized Jørgensen-Hayashi catalysts, affording 5-hydroxyisoxazolidines as single diastereoisomers with high enantioselectivities and good yields (up to 83% yield, up to 99% ee). |
Publication date:
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2018-08-06 |
Subject(s):
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54 |
Rights:
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You have selected the Attribution-NonCommercial-NoDerivatives 4.0 International License.
This license is permanently located at
http://creativecommons.org/licenses/by-nc-nd/4.0/. |
Pages:
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2914 p. |
Document type:
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Article Article - Accepted version |
DOI:
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10.1002/adsc.201800572
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