Continuous-flow enantioselective α-aminoxylation of aldehydes catalyzed by a polystyrene-immobilized hydroxyproline

Scholarly Works

• Zhou, Z.; Kasten, K.; Kang, T.; Cordes, D. B.; Smith, A. D. Enantioselective Synthesis in Continuous Flow: Polymer-Supported Isothiourea-Catalyzed Enantioselective Michael Addition-Cyclization with α-Azol-2-ylacetophenones. Organic process research & development 2024, 28, 2041–2049. doi:10.1021/acs.oprd.4c00113
• Waghmode, S. B.; Jadhao, A. R. Organocatalytic Approach to the Enantioselective Total Synthesis of (+)-Serinolamides A and B and (+)-Lacosamide. Synthesis 2023, 56, 1407–1414. doi:10.1055/a-2222-3822
• Rodríguez‐Escrich, C.; Pericàs, M. A. doi:10.1002/9783527832217.ch11
• Ötvös, S. B.; Kappe, C. O. Continuous flow asymmetric synthesis of chiral active pharmaceutical ingredients and their advanced intermediates. Green chemistry : an international journal and green chemistry resource : GC 2021, 23, 6117–6138. doi:10.1039/d1gc01615f
• Chevis, P. J.; Pyne, S. G. Synthesis of enantioenriched α-heteroatom functionalised aldehydes by chiral organocatalysis and their synthetic applications. Organic Chemistry Frontiers 2021, 8, 2287–2314. doi:10.1039/d1qo00101a
• Schmiegel, C. J.; Baier, R.; Kuckling, D. Direct Asymmetric Aldol Reaction in Continuous Flow Using Gel-Bound Organocatalysts. European Journal of Organic Chemistry 2021, 2021, 2578–2586. doi:10.1002/ejoc.202100268
• Schmiegel, C. J.; Berg, P.; Obst, F.; Schoch, R.; Appelhans, D.; Kuckling, D. Continuous Flow Synthesis of Azoxybenzenes by Reductive Dimerization of Nitrosobenzenes with Gel-Bound Catalysts. European Journal of Organic Chemistry 2021, 2021, 1628–1636. doi:10.1002/ejoc.202100006
• Okuno, Y.; Shibata, T.; Ohyou, A.; Suzuki, R.; Takegami, M.; Kato, S.; Isomura, S.; Aoki, S.; Kanno, J.; Sato, Y. Synthesis of Bi-functional Immobilized Polymer Catalysts via a Two-step Radiation-induced Graft Polymerization Process. ChemCatChem 2020, 13, 1498–1502. doi:10.1002/cctc.202001451
• Ötvös, S. B.; Llanes, P.; Pericàs, M. A.; Kappe, C. O. Telescoped Continuous Flow Synthesis of Optically Active γ-Nitrobutyric Acids as Key Intermediates of Baclofen, Phenibut, and Fluorophenibut. Organic letters 2020, 22, 8122–8126. doi:10.1021/acs.orglett.0c03100
• Berg, P.; Obst, F.; Simon, D.; Richter, A.; Appelhans, D.; Kuckling, D. Novel Application of Polymer Networks Carrying Tertiary Amines as a Catalyst Inside Microflow Reactors Used for Knoevenagel Reactions. European Journal of Organic Chemistry 2020, 2020, 5765–5774. doi:10.1002/ejoc.202000978
• Yoo, W.-J.; Ishitani, H.; Saito, Y.; Laroche, B.; Kobayashi, S. Reworking Organic Synthesis for the Modern Age: Synthetic Strategies Based on Continuous-Flow Addition and Condensation Reactions with Heterogeneous Catalysts. The Journal of organic chemistry 2020, 85, 5132–5145. doi:10.1021/acs.joc.9b03416
• Ötvös, S. B.; Pericàs, M. A.; Kappe, C. O. Multigram-scale flow synthesis of the chiral key intermediate of (-)-paroxetine enabled by solvent-free heterogeneous organocatalysis. Chemical science 2019, 10, 11141–11146. doi:10.1039/c9sc04752b
• Rodríguez-Escrich, C.; Pericàs, M. A. Catalytic Enantioselective Flow Processes with Solid-Supported Chiral Catalysts. Chemical record (New York, N.Y.) 2018, 19, 1872–1890. doi:10.1002/tcr.201800097
• Masuda, K.; Ichitsuka, T.; Koumura, N.; Sato, K.; Kobayashi, S. Flow fine synthesis with heterogeneous catalysts. Tetrahedron 2018, 74, 1705–1730. doi:10.1016/j.tet.2018.02.006
• Mastalir, Á.; Bartók, M. Handbook of Solid State Chemistry; Wiley, 2017; pp 479–509. doi:10.1002/9783527691036.hsscvol6030
• Jain, V. K.; Ramapanicker, R. Diastereoselective synthesis of D-threo-sphinganine, L-erythro-sphinganine and (−)-spisulosine through asymmetric α-hydroxylation of a higher homologue of Garner's aldehyde. Tetrahedron 2017, 73, 1568–1575. doi:10.1016/j.tet.2017.02.001
• Philip, A. T.; Raju, E.; Ramapanicker, R. Stereoselective Synthesis of Hydroxy Diamino Acid Derivatives and the Caprolactam Unit of Bengamide A through Organocatalytic α-Hydroxylation and Reductive Amination of Aldehydes. European Journal of Organic Chemistry 2016, 2016, 5502–5510. doi:10.1002/ejoc.201600842
• Chacko, S.; Ramapanicker, R. Synthesis of 1-Deoxy-8,8a–di–epi–castanospermine, 1-Deoxy-6,7,8a–tri–epi–castanospermine and Formal Synthesis of Pumilotoxin 251D. ChemistrySelect 2016, 1, 4458–4462. doi:10.1002/slct.201600891
• Etayo, P.; Ayats, C.; Pericàs, M. A. Synthesis and catalytic applications of C3-symmetric tris(triazolyl)methanol ligands and derivatives. Chemical communications (Cambridge, England) 2016, 52, 1997–2010. doi:10.1039/c5cc08961a
• Ötvös, S. B.; Szloszár, A.; Mándity, I. M.; Fülöp, F. Heterogeneous Dipeptide-Catalyzed α-Amination of Aldehydes in a Continuous-Flow Reactor: Effect of Residence Time on Enantioselectivity. Advanced Synthesis & Catalysis 2015, 357, 3671–3680. doi:10.1002/adsc.201500375

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