Starting from chiral-protected 4-hydroxymethyl pyrrolidin-2-ones, the otherwise elusive 3,4-trans-3,3,4-trisubstituted isosteres of alpha-methyl homoserine, tethered on a gamma-lactam ring, were prepared exploiting stereoselective electrophilic aminations. These reactions led to the isolation and characterization of a novel type of atropisomers, exceedingly stable at room temperature, that were directly converted to the desired products by a novel non-reductive N-N bond cleavage reaction.
Highly stable atropisomers by electrophilic amination of a chiral γ-lactam within the synthesis of an elusive conformationally restricted analogue of α-methylhomoserine / Amabili, Paolo; Amici, Adolfo; Civitavecchia, Annafelicia; Maggiore, Beatrice; Orena, Mario; Rinaldi, Samuele; Tolomelli, Alessandra. - In: AMINO ACIDS. - ISSN 0939-4451. - STAMPA. - 48:2(2016), pp. 461-478. [10.1007/s00726-015-2100-4]
Highly stable atropisomers by electrophilic amination of a chiral γ-lactam within the synthesis of an elusive conformationally restricted analogue of α-methylhomoserine
AMABILI, PAOLO;AMICI, Adolfo;CIVITAVECCHIA, ANNAFELICIA;MAGGIORE, BEATRICE;ORENA, MARIO;RINALDI, SAMUELE
;TOLOMELLI, ALESSANDRA
2016-01-01
Abstract
Starting from chiral-protected 4-hydroxymethyl pyrrolidin-2-ones, the otherwise elusive 3,4-trans-3,3,4-trisubstituted isosteres of alpha-methyl homoserine, tethered on a gamma-lactam ring, were prepared exploiting stereoselective electrophilic aminations. These reactions led to the isolation and characterization of a novel type of atropisomers, exceedingly stable at room temperature, that were directly converted to the desired products by a novel non-reductive N-N bond cleavage reaction.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.