Journal
SYNLETT
Volume 24, Issue 16, Pages 2160-2164Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0033-1339497
Keywords
axially unfixed biaryl; water; organocatalysts; aldol reaction; stereoselectivity
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Funding
- Beijing Municipal Commission of Education [JC015001200902]
- Beijing Municipal Natural Science Foundation [7102010, 2122008]
- Basic Research Foundation of Beijing University of Technology [X4015001201101]
- Funding Project for Academic Human Resources Development in Institutions of Higher Learning Under the Jurisdiction of Beijing Municipality [PHR201008025]
- Doctoral Scientific Research Start-up Foundation of Beijing University of Technology [52015001200701]
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A family of novel axially unfixed biaryl-based, water-compatible bifunctional organocatalysts were designed and synthesized for asymmetric catalytic direct aldol reactions in water. These organocatalysts are comprised of prolinamide, aromatic sulfonamide and biaryl motifs. Under the optimal reaction conditions, one organocatalyst in particular delivered excellent stereocontrol (up to 99% ee and 99:1 dr) in direct aldol reactions of cyclohexanone with a variety of aromatic aldehydes in water.
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