A New Synthetic Method of 1,5-Dimethyl-3-Oxabicyclo[3.1.0] Hexane-2,4-Dione
Youcef Mechehoud1, Nadjah Belattar1, *, Samir Benayache1, Fadila Benayache1, Paul Mosset2
Identifiers and Pagination:Year: 2018
First Page: 44
Last Page: 50
Publisher Id: CHEM-5-44
Article History:Received Date: 09/03/2018
Revision Received Date: 10/05/2018
Acceptance Date: 31/05/2018
Electronic publication date: 29/06/2018
Collection year: 2018
open-access license: This is an open access article distributed under the terms of the Creative Commons Attribution 4.0 International Public License (CC-BY 4.0), a copy of which is available at: https://creativecommons.org/licenses/by/4.0/legalcode. This license permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.
We have described in this reported work a new method in the synthesis of cis-1,5-dimethyl -3-oxabicyclo [3.1.0] hexane-2,4-dione in good yield.
Optimization of practical conditions leads to obtain 1,3-cyclopropanedicarboxylic anhydrides as important precursors of functionalized cyclopropane derivatives.
The condensation of 2-chloropropanoic acid with ethyl methacrylate using (2M) LDA dissolved in hexane and THF at (-80°C), and the treatment with acetyl chloride permit to obtain the substituted 1,3- cyclopropanedicarboxylic anhydride .
We have proceeded to the synthesis of cis-1,5-dimethyl -3-oxabicyclo [3.1.0] hexane-2,4-dione as functionalized organic compound with high efficiency ,taking into account the regioselectivity of carbanion attack to double bond activated by an electrophilic group.
Using (2M) LDA dissolved in hexane and THF at (-80°C) is a good way to afford the enantioselective substituted 1,3- cyclopropanedicarboxylic anhydrides.