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https://hdl.handle.net/1959.11/19512
Title: | Chemo-Enzymatic Synthesis of Chiral Epoxides Ethyl and Methyl (S)-3-(Oxiran-2-yl)propanoates from Renewable Levoglucosenone: An Access to Enantiopure (S)-Dairy Lactone | Contributor(s): | Peru, Aurelien A M (author); Flourat, Amandine L (author); Gunawan, Christian (author); Raverty, Warwick (author); Jevric, Martyn (author); Greatrex, Ben (author) ; Allais, Florent (author) | Publication Date: | 2016 | Open Access: | Yes | DOI: | 10.3390/molecules21080988 | Handle Link: | https://hdl.handle.net/1959.11/19512 | Abstract: | Chiral epoxides-such as ethyl and methyl (S)-3-(oxiran-2-yl)propanoates ((S)-1a/1b)-are valuable precursors in many chemical syntheses. Until recently, these compounds were synthesized from glutamic acid in four steps (deamination, reduction, tosylation and epoxide formation) in low to moderate overall yield (20%-50%). Moreover, this procedure requires some harmful reagents such as sodium nitrite ((eco)toxic) and borane (carcinogen). Herein, starting from levoglucosenone (LGO), a biobased chiral compound obtained through the flash pyrolysis of acidified cellulose, we propose a safer and more sustainable chemo-enzymatic synthetic pathway involving lipase-mediated Baeyer-Villiger oxidation, palladium-catalyzed hydrogenation, tosylation and treatment with sodium ethoxide/methoxide as key steps. This route afforded ethyl and methyl (S)-3-(oxiran-2-yl)propanoates in 57% overall yield, respectively. To demonstrate the potentiality of this new synthetic pathway from LGO, the synthesis of high value-added (S)-dairy lactone was undertaken from these epoxides and provided the target in 37% overall yield from LGO. | Publication Type: | Journal Article | Source of Publication: | Molecules, 21(8), p. 1-10 | Publisher: | MDPI AG | Place of Publication: | Switzerland | ISSN: | 1420-3049 1431-5165 |
Fields of Research (FoR) 2008: | 030503 Organic Chemical Synthesis 030599 Organic Chemistry not elsewhere classified 030504 Organic Green Chemistry |
Fields of Research (FoR) 2020: | 340503 Organic chemical synthesis 340504 Organic green chemistry |
Socio-Economic Objective (SEO) 2008: | 860604 Organic Industrial Chemicals (excl. Resins, Rubber and Plastics) 970103 Expanding Knowledge in the Chemical Sciences |
Socio-Economic Objective (SEO) 2020: | 240908 Organic industrial chemicals (excl. resins, rubber and plastics) 280105 Expanding knowledge in the chemical sciences |
Peer Reviewed: | Yes | HERDC Category Description: | C1 Refereed Article in a Scholarly Journal |
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Appears in Collections: | Journal Article School of Rural Medicine |
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