- Abstract:
- 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.
- Publication status:
- Published
- Peer review status:
- Peer Reviewed
- Version:
- Submitted Manuscript
- Files:
-
-
(pdf, 434.5kb)
-
- Publisher copy:
- 10.1021/ol303271z
-
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- Journal:
- Organic Letters
- Volume:
- 15
- Issue:
- 2
- Pages:
- 346-349
- Publication date:
- 2013-01-03
- DOI:
- EISSN:
-
1523-7052
- ISSN:
-
1523-7060
- URN:
-
uuid:65b4d86f-7372-4783-910c-62ad4b71089b
- Source identifiers:
-
374214
- Local pid:
- pubs:374214
- Language:
- English
- Keywords:
- Copyright holder:
- American Chemical Society
- Copyright date:
- 2013
- Notes:
- 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
Journal article
Control of phosphoryl migratory transesterifications allows regioselecive access to sugar phosphates.
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International AIDS Vaccine Initiative
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