Control of phosphoryl migratory transesterifications allows regioselecive access to sugar phosphates.
- Phosphate esters in polyhydroxylated systems are normally blighted by uncontrolled migration under a variety of reaction conditions. Cesium fluoride is demonstrated as a reagent to control migration of primary phosphates during transesterifications. This allows easy exchange of phosphoryl protecting groups enabling enhanced synthetic strategic flexibility and regioselective phosphate installation. Mechanistic analysis suggests that a fluoride-induced extended solvent sphere modulates steric bulk at phosphorus to favor the primary position.
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- Peer review status:
- Peer Reviewed
- Submitted Manuscript
- Copyright holder:
- American Chemical Society
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- This document is the unedited author's version of a Submitted Work that was subsequently accepted for publication in Organic Letters, copyright © American Chemical Society after peer review. To access the final edited and published work, see http://pubs.acs.org/doi/abs/10.1021/ol303271z
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