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Thermoresponsive polymer-supportedl-proline micelle catalysts for thedDirect asymmetric aldol reaction in water
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Zayas, Hazit A., Lu, Annhelen, Valade, David, Amir, Faheem, Jia, Zhongfan, O’Reilly, Rachel K. and Monteiro, Michael J. (2013) Thermoresponsive polymer-supportedl-proline micelle catalysts for thedDirect asymmetric aldol reaction in water. ACS Macro Letters, Volume 2 (Number 4). pp. 327-331. doi:10.1021/mz4000943 ISSN 2161-1653.
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Official URL: http://dx.doi.org/10.1021/mz4000943
Abstract
l-Proline moieties bound to a thermoresponsive polymer nanoreactor efficiently directed the asymmetric aldol reaction in water with excellent yields and enantioselectivity (ee). The reactions were efficient at higher temperatures in direct contrast to the low yields and ee values found when the reaction was carried out in a DMF/water mixture due to the location of the l-proline moieties within the hydrophobic pocket inside the core of the nanoreactors. This ideal environment formed for catalysis allows control over the water content as well as enhancing interactions between the carboxylic acid of l-proline and the aldehyde substrate. The nanoreactors were disassembled to fully water-soluble polymers by lowering the temperature to below the lower critical solution temperature (LCST) of the polymer, resulting in precipitation of the product in near pure form. The product was isolated by centrifugation and the polymer/water solution reused in additional catalytic cycles by heating the polymer above its LCST and thus reforming the nanoreactors. Although a small decrease in yield after five cycles was observed, the selectivity (anti/syn ratio and ee) remained high.
Item Type: | Journal Article | ||||
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Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||
Journal or Publication Title: | ACS Macro Letters | ||||
Publisher: | American Chemical Society | ||||
ISSN: | 2161-1653 | ||||
Official Date: | 2013 | ||||
Dates: |
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Volume: | Volume 2 | ||||
Number: | Number 4 | ||||
Page Range: | pp. 327-331 | ||||
DOI: | 10.1021/mz4000943 | ||||
Status: | Peer Reviewed | ||||
Publication Status: | Published | ||||
Access rights to Published version: | Restricted or Subscription Access |
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