Organocatalytic Packed-Bed Reactors for the Enantioselective Flow Synthesis of Quaternary Isotetronic Acids by Direct Aldol Reactions of Pyruvates
The utilization of the homogeneous (<i>S</i>)-2-pyrrolidine-tetrazole organocatalyst (Ley catalyst) in the self-condensation of ethyl pyruvate and cross-aldol reactions of ethyl pyruvate donor with non-enolizable pyruvate acceptors, namely the sterically hindered ethyl 3-methyl-2-oxobuty...
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MDPI AG
2025-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/30/2/296 |
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| author | Lorenzo Poletti Carmela De Risi Daniele Ragno Graziano Di Carmine Riccardo Tassoni Alessandro Massi Paolo Dambruoso |
| author_facet | Lorenzo Poletti Carmela De Risi Daniele Ragno Graziano Di Carmine Riccardo Tassoni Alessandro Massi Paolo Dambruoso |
| author_sort | Lorenzo Poletti |
| collection | DOAJ |
| description | The utilization of the homogeneous (<i>S</i>)-2-pyrrolidine-tetrazole organocatalyst (Ley catalyst) in the self-condensation of ethyl pyruvate and cross-aldol reactions of ethyl pyruvate donor with non-enolizable pyruvate acceptors, namely the sterically hindered ethyl 3-methyl-2-oxobutyrate or the highly electrophilic methyl 3,3,3-trifluoropyruvate, is described as the key enantioselective step toward the synthesis of the corresponding biologically relevant isotetronic acids featuring a quaternary carbon functionalized with ester and alkyl groups. The transition from homogeneous to heterogeneous flow conditions is also investigated, detailing the fabrication and operation of packed-bed reactors filled with a silica-supported version of the pyrrolidine-tetrazole catalyst (SBA-15 as the matrix). |
| format | Article |
| id | doaj-art-183531f9dccb48809849c5025f0895ed |
| institution | Kabale University |
| issn | 1420-3049 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj-art-183531f9dccb48809849c5025f0895ed2025-01-24T13:43:27ZengMDPI AGMolecules1420-30492025-01-0130229610.3390/molecules30020296Organocatalytic Packed-Bed Reactors for the Enantioselective Flow Synthesis of Quaternary Isotetronic Acids by Direct Aldol Reactions of PyruvatesLorenzo Poletti0Carmela De Risi1Daniele Ragno2Graziano Di Carmine3Riccardo Tassoni4Alessandro Massi5Paolo Dambruoso6Department of Environmental and Prevention Sciences, University of Ferrara, Via L. Borsari, 46, 44121 Ferrara, ItalyDepartment of Chemical, Pharmaceutical and Agricultural Sciences, University of Ferrara, Via L. Borsari, 46, 44121 Ferrara, ItalyDepartment of Chemical, Pharmaceutical and Agricultural Sciences, University of Ferrara, Via L. Borsari, 46, 44121 Ferrara, ItalyDepartment of Environmental and Prevention Sciences, University of Ferrara, Via L. Borsari, 46, 44121 Ferrara, ItalyInstitute for Organic Synthesis and Photoreactivity of the Italian National Research Council, Area della Ricerca di Bologna, Via P. Gobetti, 101, 40129 Bologna, ItalyDepartment of Chemical, Pharmaceutical and Agricultural Sciences, University of Ferrara, Via L. Borsari, 46, 44121 Ferrara, ItalyInstitute for Organic Synthesis and Photoreactivity of the Italian National Research Council, Area della Ricerca di Bologna, Via P. Gobetti, 101, 40129 Bologna, ItalyThe utilization of the homogeneous (<i>S</i>)-2-pyrrolidine-tetrazole organocatalyst (Ley catalyst) in the self-condensation of ethyl pyruvate and cross-aldol reactions of ethyl pyruvate donor with non-enolizable pyruvate acceptors, namely the sterically hindered ethyl 3-methyl-2-oxobutyrate or the highly electrophilic methyl 3,3,3-trifluoropyruvate, is described as the key enantioselective step toward the synthesis of the corresponding biologically relevant isotetronic acids featuring a quaternary carbon functionalized with ester and alkyl groups. The transition from homogeneous to heterogeneous flow conditions is also investigated, detailing the fabrication and operation of packed-bed reactors filled with a silica-supported version of the pyrrolidine-tetrazole catalyst (SBA-15 as the matrix).https://www.mdpi.com/1420-3049/30/2/296flow chemistryorganocatalysisaldol reactionbutenolidespyruvates |
| spellingShingle | Lorenzo Poletti Carmela De Risi Daniele Ragno Graziano Di Carmine Riccardo Tassoni Alessandro Massi Paolo Dambruoso Organocatalytic Packed-Bed Reactors for the Enantioselective Flow Synthesis of Quaternary Isotetronic Acids by Direct Aldol Reactions of Pyruvates Molecules flow chemistry organocatalysis aldol reaction butenolides pyruvates |
| title | Organocatalytic Packed-Bed Reactors for the Enantioselective Flow Synthesis of Quaternary Isotetronic Acids by Direct Aldol Reactions of Pyruvates |
| title_full | Organocatalytic Packed-Bed Reactors for the Enantioselective Flow Synthesis of Quaternary Isotetronic Acids by Direct Aldol Reactions of Pyruvates |
| title_fullStr | Organocatalytic Packed-Bed Reactors for the Enantioselective Flow Synthesis of Quaternary Isotetronic Acids by Direct Aldol Reactions of Pyruvates |
| title_full_unstemmed | Organocatalytic Packed-Bed Reactors for the Enantioselective Flow Synthesis of Quaternary Isotetronic Acids by Direct Aldol Reactions of Pyruvates |
| title_short | Organocatalytic Packed-Bed Reactors for the Enantioselective Flow Synthesis of Quaternary Isotetronic Acids by Direct Aldol Reactions of Pyruvates |
| title_sort | organocatalytic packed bed reactors for the enantioselective flow synthesis of quaternary isotetronic acids by direct aldol reactions of pyruvates |
| topic | flow chemistry organocatalysis aldol reaction butenolides pyruvates |
| url | https://www.mdpi.com/1420-3049/30/2/296 |
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