Effect of additives on the proline-catalyzed ketone–aldehyde aldol reactions |
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| Institution: | 1. Technische Universität Dresden, Institute of Microbiology, Chair of Molecular Biotechnology, Zellescher Weg 20b, 01217 Dresden, Germany;2. HTW Berlin—University of Applied Science, Engineering II, School of Life Science Engineering, Wilhelminenhofstr. 75A, 12459 Berlin, Germany;3. DECHEMA Forschungsinstitut, Biochemical Engineering, Theodor-Heuss-Allee 25, 60486 Frankfurt, Germany;1. Zhejiang Provincial Engineering Research Center for Green and Low-carbon Dyeing & Finishing, Eco-Dyeing and Finishing Engineering Research Center, Ministry of Education, National Base for International Science and Technology Cooperation in Textiles and Consumer-Goods Chemistry, Zhejiang Sci-Tech University, Hangzhou, 310018, China;2. Biomass Molecular Engineering Center, Department of Materials Science and Engineering, Anhui Agricultural University, Hefei, 230036, China;1. Institute of Microbiology, Chair of Molecular Biotechnology, Technische Universität Dresden, 01062 Dresden, Germany;2. Sustainable Momentum, SL Ap. Correos 3517. 35004, Las Palmas de Gran Canaria, Canary Islands, Spain;3. Center for Environmentally Beneficial Catalysis, The University of Kansas, Lawrence, KS 66047, United States;4. Biocatalysis Group, Department of Biotechnology, Delft University of Technology, Julianalaan 136, 2628 BL Delft, The Netherlands;1. Laboratory of Adsorption and Catalysis, University of Antwerp, Universiteitsplein 1, 2610 Wilrijk, Belgium;2. Department of Materials, Textiles and Chemical Engineering, Industrial Catalysis and Adsorption Technology, Ghent University, Ghent, Belgium;3. Department of Materials, Textiles and Chemical Engineering, Laboratory for Chemical Technology, Ghent University, Ghent, Belgium;4. Flemish Institute for Technological Research (VITO N.V.), Boeretang 200, 2400 Mol, Belgium;5. Department of Inorganic Chemistry and Technology, National Institute of Chemistry, Hajdrihova 19, SI-1001 Ljubljana, Slovenia;6. Centre for Ordered Materials, Organometallics & Catalysis, Ghent University, Krijgslaan 281 (S3), 9000 Ghent, Belgium;1. Departamento de Química, Centro de Investigación y de Estudios Avanzados, Instituto Politécnico Nacional, Avenida IPN No. 2508, 07360, Ciudad de México, Mexico;2. El Colegio Nacional, Luis González Obregón No. 23, Centro Histórico, 06020, Ciudad de México, Mexico |
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| Abstract: | The effect of bases, acids, and water as additives in proline-catalyzed ketone–aldehyde aldol reactions has been studied. While the reaction appears to be relatively tolerant to small amounts of tertiary amine bases or weak acids, it stops completely with strong acids. The use of water as an additive had a highly beneficial effect on reactions that were conducted with a stoichiometric ratio of ketone to aldehyde, especially with cyclic ketones. This allows the efficient use of more precious ketones such as 4-thianone as donors in the direct enantioselective aldol and facilitates purification. |
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