Abstract
Theregioselectivity of intramolecular 1,3-dipolar cycloadditions of nitrile oxides prepared from 3-O-alkenyl-1,2-O-isopropylidene-α-D- pentodialdofuranoses is dependent on the length of the alkenyl chain. 3-O-Homoallyl nitrile oxide afforded exo-cyclization oxepane exclusively. 3-O-Pentenyl nitrile oxide produced a mixture of exo- and endo-cyclization adducts (oxocane and oxonane) whereas 3-O-hexenyl, heptenyl, and octenyl oxides all gave endo-cyclization adducts (ten-, eleven-, and twelve-membered cyclic ethers, respectively) exclusively.
Original language | English |
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Pages (from-to) | 1205-1208 |
Number of pages | 4 |
Journal | Synlett |
Issue number | 8 |
DOIs | |
Publication status | Published - 2006 May 15 |
Externally published | Yes |
Keywords
- Carbohydrates
- Cycloadditions
- Ethers
- Nitrile oxides
- Stereoselective synthesis
ASJC Scopus subject areas
- Organic Chemistry