Trans N-benzyl-3-trifluoromethyl-2-ethoxycarbonylaziridine 2a, easily obtainable in enantiopure form by CAl catalyzed enzymatic resolution, allowed the regio and stereoselective synthesis of fluorinated anti-alpha-functionalized -beta-aminoacids, such as trifluoroisoserinates ar trifluoro-beta-alanine, and trans 3-halo or 3-hydroxy-beta-lactams. Starting from the anantiomerically pure methyl analogue of the title compound, pure enantiomers of trifluoroisoserine can be obtained in high overall chemical yield. Absolute configurations of optically-pure beta-aminoacids were determined by chemical correlation.
Stereoselective Synthesis of Fluorinated β-Aminoacids from Ethyl trans-N-Benzyl-3-Trifluoromethyl-Aziridine-2-Carboxylate / Davoli, Paolo; Forni, Arrigo; Franciosi, Chiara; Moretti, Irene; Prati, Fabio. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - STAMPA. - 10:(1999), pp. 2361-2371.
Stereoselective Synthesis of Fluorinated β-Aminoacids from Ethyl trans-N-Benzyl-3-Trifluoromethyl-Aziridine-2-Carboxylate
DAVOLI, Paolo;FORNI, Arrigo;FRANCIOSI, Chiara;MORETTI, Irene;PRATI, Fabio
1999
Abstract
Trans N-benzyl-3-trifluoromethyl-2-ethoxycarbonylaziridine 2a, easily obtainable in enantiopure form by CAl catalyzed enzymatic resolution, allowed the regio and stereoselective synthesis of fluorinated anti-alpha-functionalized -beta-aminoacids, such as trifluoroisoserinates ar trifluoro-beta-alanine, and trans 3-halo or 3-hydroxy-beta-lactams. Starting from the anantiomerically pure methyl analogue of the title compound, pure enantiomers of trifluoroisoserine can be obtained in high overall chemical yield. Absolute configurations of optically-pure beta-aminoacids were determined by chemical correlation.
Pubblicazioni consigliate
I metadati presenti in IRIS UNIMORE sono rilasciati con licenza Creative Commons CC0 1.0 Universal, mentre i file delle pubblicazioni sono rilasciati con licenza Attribuzione 4.0 Internazionale (CC BY 4.0), salvo diversa indicazione.
In caso di violazione di copyright, contattare Supporto Iris
