Please use this identifier to cite or link to this item: https://hdl.handle.net/1959.11/60119
Title: New chemo-enzymatic route for the synthesis of chiral glycidyl esters ((S)-ethyl and (S)-methyl-4,5-epoxypentanoates) from renewable resources
Contributor(s): Peru, Aurélien (author); Flourat, Amandine (author); Duncan, Anthony (author); Raverty, Warwick (author); Greatrex, Ben  (author)orcid ; Allais, Florent (author)
Publication Date: 2016-08-18
Open Access: Yes
Handle Link: https://hdl.handle.net/1959.11/60119
Open Access Link: https://scimeetings.acs.org/exhibit/New-chemo-enzymatic-route-synthesis/2502660Open Access Link
Abstract: 

Chiral glycidyl esters – such as (S)-ethyl- or (S)-methyl-4,5-epoxypentanoates - 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 average global yield (20-50%). Moreover, this procedure requires some harmful reagents such as sodium nitrite (toxic and ecotoxic) and boron hydride (carcinogen).

Herein, to access these chiral glycidyl esters, we propose a safer chemo-enzymatic synthetic pathway starting from levoglucosenone (aka LGO, CAS 37112-31-5), a biobased compound obtained through the flash pyrolysis of cellulose. Firstly, LGO was submitted to a lipase-mediated Baeyer-Villiger oxidation followed by an acidic hydrolysis to afford (S)-γ-hydroxymethyl-α,β-butenolide. The latter then underwent a palladium-catalyzed hydrogenation to give (S)-γ-hydroxymethyl-γ-butyrolactone. Finally, after tosylation, the corresponding intermediate was treated with sodium ethoxide/methoxide to afford (S)-Ethyl and (S)-Methyl-4,5-epoxypentanoates in 57% yield, respectively.

Publication Type: Conference Publication
Conference Details: ACS 2016: 252nd American Chemical Society National Meeting & Exposition, Philadelphia, Pennsylvania, United States of America, 21st -26th August, 2016
Source of Publication: 252nd American Chemical Society National Meeting and Exposition, Chemistry of People, by the People, for the People, v.252
Publisher: American Chemical Society
Place of Publication: United States of America
ISSN: 0065-7727
Fields of Research (FoR) 2020: 340503 Organic chemical synthesis
340504 Organic green chemistry
Socio-Economic Objective (SEO) 2020: 280105 Expanding knowledge in the chemical sciences
240904 Fine chemicals
HERDC Category Description: E5 Conference Poster
Publisher/associated links: https://www.acs.org/meetings/acs-meetings/past-meetings.html
Appears in Collections:Conference Publication
School of Rural Medicine

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