Synthesis of 2,3-trans disubstituted tetrahydrofurans through sequential xanthate radical addition-substitution reactions.
A two-step preparation of 2,3-trans disubstituted tetrahydrofuran derivatives is reported from S-alkyl dithiocarbonates. The study of the group transfer reaction from xanthates and alkenes afforded intermediate S-alkyl dithiocarbonates. From 2,3-dihydrofuran derivatives, the displacement of the resulting anomeric xanthates with various nucleophiles in the presence of Lewis acid allowed the formation of new carbon-carbon and carbon-heteroatom bonds. This strategy was illustrated by a two-step synthesis of a precursor of modified 2'-beta-C-branched nucleoside analogues.
Jean-Baptiste
Laëtitia
L
Laboratoire de Chimie Moléculaire et Thioorganique, UMR CNRS 6507; ENSICAEN-Université de Caen, 6 Boulevard du Maréchal Juin, F-14050 Caen Cedex, France.
Yemets
Sergiy
S
Legay
Rémi
R
Lequeux
Thierry
T
D000475:Alkenes / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D014966:Xanthenes / Q000737:chemistry*
D000475:Alkenes; D005609:Free Radicals; D005663:Furans; D014966:Xanthenes