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 / Amabili, Paolo; Amici, Adolfo; Campisi, Giovanni; Guerra, Giulia; Monari, Magda; Orena, Mario; Piccinelli, Fabio; Rinaldi, Samuele; Tolomelli, Alessandra. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - ELETTRONICO. - 2018:46(2018), pp. 6524-6536. [10.1002/ejoc.201801213]
Synthesis of Enantiopure Isosteres of Amino Acids Containing a Quaternary Stereocenter: Experimental and Computational Evaluation of a Novel Class of Atropisomers
Amabili, Paolo;Amici, Adolfo;GUERRA, GIULIA;Orena, Mario;Rinaldi, Samuele
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2018-01-01
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
