Synthesis and N-functionalization of isoxazolidines: a new approach to nucleoside analogues

• Type: Article in International Scientific Journal
• Date: 2014

Authors

Carlos A D Sousa (Author) Other; Jose E Rodriguez Borges (Author) FCUP; Xerardo Garcia Mera (Author) Other

Journal

Title: Tetrahedron Letters

Vol. 55

Pages: 4628-4631

ISSN: 0040-4039

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 2 Citations

Scopus - 3 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: P-009-RM3

DOI: 10.1016/j.tetlet.2014.06.076

Abstract (EN): A straightforward synthetic approach for the preparation of non N-functionalized isoxazolidines from BF3-catalyzed 1,3-cycloaddition reactions between methyl glyoxylate oxime and alkenes is described. Subsequently, isoxazolidines were N-functionalized with three chemically active groups (2-chloroethyl, cyanomethyl and 2-acetoxyethyl), thus allowing the preparation of a wide array of N-functionalized isoxazolidines. The compounds were characterized by means of H-1 and C-13 NMR spectroscopy and mass spectrometry. X-ray analysis was used for stereochemical elucidation.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 4