Journal
GREEN CHEMISTRY
Volume 23, Issue 19, Pages 7773-7779Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1gc02831f
Keywords
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Funding
- China National Natural Science Foundation [22071154, 22001171]
- Shanghai Sciences and Technologies Development Fund [20070502600]
- Shanghai Sailing Program [2020YF1435200]
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The development of a combination enzyme and organocatalyst for aqueous sequential organic transformation is environmentally friendly and overcomes the drawback of only a single methodological approach. The integrated laccase and proline as a chemo-enzymatic co-catalyst system enables efficient oxidation/aldol enantioselective sequential reaction, providing various 1,2-diastereoisomeric chiral beta-hydroxy ketones with acceptable yields and high enantio-/diastereoselectivities.
The development of a combination enzyme and organocatalyst for aqueous sequential organic transformation has great significance, in that it is not only environmentally friendly but also overcomes only a single methodological drawback, either in the chemical or biological process. Herein, through the utilization of the bulky steric hindrance of chiral proline derivatives, an integrated laccase and proline as a chemo-enzymatic co-catalyst system is developed. It enables an efficient oxidation/aldol enantioselective sequential reaction to be accomplished, overcoming the mutual deactivation issue. As we present in this study, this one-pot organic transformation, an initial laccase-mediated oxidation of arylbenzyl alcohols and cyclohexanol to form aldehydes and cyclohexanone, followed by a subsequent proline derivative-catalyzed aldol condensation of the in situ generated intermediates, provides various 1,2-diastereoisomeric chiral beta-hydroxy ketones with acceptable yields and high enantio-/diastereoselectivities.
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