Polymer-supported synthesis of 2,5-disubstituted tetrahydrofurans via tandem 1,3-dipolar cycloaddition/electrophilic cyclization has been accomplished using a five-step reaction sequence to give 2-(cyanomethyl)-5-(iodomethyl)tetrahydrofuran (cis:trans ratio of 1:2) in 40% overall yield. The corresponding 2-(cyanomethyl)-6-(iodomethyl)tetrahydropyran was similarly formed in a 7% overall yield. The final electrophilic cyclization simultaneously releases the desired product and regenerates the initial polymer-bound functionality. In the process the desired cyclic ether is obtained exclusively; byproducts of the sequence are not cleaved from the polymer support. In addition the polymer support is sufficiently robust to be recovered and recycled through the reaction sequence.
|Original language||English (US)|
|Number of pages||8|
|Journal||Journal of Organic Chemistry|
|State||Published - 1995|
ASJC Scopus subject areas
- Organic Chemistry