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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)orcid ; Allais, Florent (author)
Publication Date: 2016
Open Access: Yes
DOI: 10.3390/molecules21080988Open Access Link
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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: MDPIAG
Place of Publication: Basel, Switzerland
ISSN: 1420-3049
Field of Research (FOR): 030503 Organic Chemical Synthesis
030599 Organic Chemistry not elsewhere classified
030504 Organic Green Chemistry
Socio-Economic Outcome Codes: 860604 Organic Industrial Chemicals (excl. Resins, Rubber and Plastics)
970103 Expanding Knowledge in the Chemical Sciences
Peer Reviewed: Yes
HERDC Category Description: C1 Refereed Article in a Scholarly Journal
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