Starting from chiral-protected 4-hydroxymethyl pyrrolidin-2-ones, the otherwise elusive 3,4-trans-3,3,4-trisubstituted isosteres of α-methyl homoserine, tethered on a γ-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 g-lactam within the synthesis of an elusive conformationally restricted analogue of a-methylhomoserine / P.Amabili, A. Amici; Civitavecchia, A.; Maggiore, B.; Orena, M.; Rinaldi, S.; A. Tolomelli. - In: AMINO ACIDS. - ISSN 0939-4451. - STAMPA. - 48://(2016), pp. 1438-2199.461-1438-2199.478. [10.1007/s00726-015-2100-4]
Highly stable atropisomers by electrophilic amination of a chiral g-lactam within the synthesis of an elusive conformationally restricted analogue of a-methylhomoserine
TOLOMELLI, ALESSANDRA
2016
Abstract
Starting from chiral-protected 4-hydroxymethyl pyrrolidin-2-ones, the otherwise elusive 3,4-trans-3,3,4-trisubstituted isosteres of α-methyl homoserine, tethered on a γ-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.
