期刊
ORGANIC LETTERS
卷 15, 期 2, 页码 346-349出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol303271z
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资金
- International AIDS Vaccine Initiative
- Royal Society
- BBSRC [BB/E004350/1] Funding Source: UKRI
- EPSRC [EP/G026688/1, EP/I500200/1, EP/E000614/1] Funding Source: UKRI
- Biotechnology and Biological Sciences Research Council [BB/C510824/1, BB/E004350/1, EGA17763] Funding Source: researchfish
- Engineering and Physical Sciences Research Council [EP/E000614/1, EP/D023335/1, GR/T26542/01, EP/G026688/1, EP/I500200/1, EP/D023343/1] Funding Source: researchfish
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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