Carbonation of natural α-amino acids in water and subsequent cyclization with (2-bromo-1-arylethyl)dimethylsulfonium bromides led selectively to a family of 2-oxazolidinonyl derivatives, which were isolated without the needing of purification. Analogous conjugation of the 2-oxazolidinone skeleton with amino acids was previously realized by complicated and narrow-scope routes, whereby the amino acid core is built stepwise. Deprotonation of some of the products afforded the corresponding water-soluble carboxylates, while a straightforward, proof of concept esterification reaction of the carboxylic acid group yielded a menthol-alanine-oxazolidinone conjugate.
Trapping carbamates of α-Amino acids: One-Pot and catalyst-free synthesis of 5-Aryl-2-Oxazolidinonyl derivatives / Bresciani G.; Zacchini S.; Famlonga L.; Pampaloni G.; Marchetti F.. - In: JOURNAL OF CO2 UTILIZATION. - ISSN 2212-9820. - ELETTRONICO. - 47:(2021), pp. 101495.1-101495.6. [10.1016/j.jcou.2021.101495]
Trapping carbamates of α-Amino acids: One-Pot and catalyst-free synthesis of 5-Aryl-2-Oxazolidinonyl derivatives
Zacchini S.;
2021
Abstract
Carbonation of natural α-amino acids in water and subsequent cyclization with (2-bromo-1-arylethyl)dimethylsulfonium bromides led selectively to a family of 2-oxazolidinonyl derivatives, which were isolated without the needing of purification. Analogous conjugation of the 2-oxazolidinone skeleton with amino acids was previously realized by complicated and narrow-scope routes, whereby the amino acid core is built stepwise. Deprotonation of some of the products afforded the corresponding water-soluble carboxylates, while a straightforward, proof of concept esterification reaction of the carboxylic acid group yielded a menthol-alanine-oxazolidinone conjugate.File | Dimensione | Formato | |
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