Electrophilic amination of diastereomeric 4-methoxycarbonyl pyrrolidin-2-ones allowed to prepare both diastereomers of an amino acid bearing a quaternary chiral center, a key intermediate to antibiotic 8-methoxyquinolone carboxylic acid. Within this synthesis, novel atropisomers, exceedingly stable at room temperature, were isolated and characterized, which were subsequently converted into the desired products by a novel reductive N–N bond cleavage reaction.

Synthesis of Enantiopure Isosteres of Amino Acids Containing a Quaternary Stereocenter: Experimental and Computational Evaluation of a Novel Class of Atropisomers

Monari, Magda;Orena, Mario;Piccinelli, Fabio;Rinaldi, Samuele
;
Tolomelli, Alessandra
2018

Abstract

Electrophilic amination of diastereomeric 4-methoxycarbonyl pyrrolidin-2-ones allowed to prepare both diastereomers of an amino acid bearing a quaternary chiral center, a key intermediate to antibiotic 8-methoxyquinolone carboxylic acid. Within this synthesis, novel atropisomers, exceedingly stable at room temperature, were isolated and characterized, which were subsequently converted into the desired products by a novel reductive N–N bond cleavage reaction.
Amabili, Paolo; Amici, Adolfo; Campisi, Giovanni; Guerra, Giulia; Monari, Magda; Orena, Mario; Piccinelli, Fabio; Rinaldi, Samuele*; Tolomelli, Alessandra
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11585/665559
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