Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2017, Issue 34, Pages 5032-5043Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201700646
Keywords
Nucleophilic substitution; Cleavage reactions; Glycerol carbonate; Glycidyl carbamates; Amines
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Funding
- Chryso(R) Company
- University of Orleans
- Conseil General du Loiret
- Region Centre Val de Loire (APR Cosmetosciences) [2016-00110369]
- LABEX SynOrg [ANR-11-LABX-0029]
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The reactivity of mesylated and tosylated glycerol carbonate towards secondary and tertiary amines has been studied, and allowed regioselective access to carbamates which could then be transformed into glycidyl carbamates. By tuning the reaction conditions, we were able to direct the reaction towards the synthesis of new 5-aminomethyldioxolan-2-one derivatives. The opening of glycidyl carbamates with various amines was also explored, and showed the opportunity to use glycerol as a linker between two different amine moieties.
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