Abstract
A two-step preparation of 2,3-trans disubstituted tetrahydrofuran derivatives is reported from 5-alkyl dithiocarbonates. The study of the group transfer reaction from xanthates and alkenes afforded intermediate 5-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′-β-C-branched nucleoside analogues.
Original language | English (US) |
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Pages (from-to) | 2352-2359 |
Number of pages | 8 |
Journal | Journal of Organic Chemistry |
Volume | 71 |
Issue number | 6 |
DOIs | |
State | Published - Mar 17 2006 |