<div class="csl-bib-body">
<div class="csl-entry">Prechelmacher, S., Mereiter, K., & Hammerschmidt, F. (2018). The α-hydroxyphosphonate-phosphate rearrangement of a noncyclic substrate - some new observations. <i>Organic and Biomolecular Chemistry</i>, <i>16</i>(19), 3672–3680. https://doi.org/10.1039/c8ob00419f</div>
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dc.identifier.issn
1477-0520
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dc.identifier.uri
http://hdl.handle.net/20.500.12708/192909
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dc.description.abstract
Racemic ethyl hydrogen (1-hydroxy-2-methylsulfanyl-1-phenylethyl)phosphonate was resolved with (R)-1-phenylethylamine. The (R)-configuration of the (-)-enantiomer was determined by chemical correlation. Esterification of the (-)-enantiomer with a substituted diazomethane derived from 3-hydroxy-1,3,5(10)-estratrien-17-one delivered two epimeric phosphonates separated by HPLC. Methylation with methyl fluorosulfate at the sulfur atom and treatment with a strong base induced an α-hydroxyphosphonate-phosphate rearrangement with formation of dimethyl sulphide and two enantiomerically pure enol phosphates. Their oily nature interfered with a single crystal X-ray structure analysis to determine the stereochemistry at the phosphorus atom.
en
dc.language.iso
en
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dc.publisher
Royal Society of Chemistry (RSC)
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dc.relation.ispartof
Organic and Biomolecular Chemistry
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dc.rights.uri
http://creativecommons.org/licenses/by/3.0/
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dc.subject
α-hydroxyphosphonate-phosphate rearrangement
en
dc.title
The α-hydroxyphosphonate-phosphate rearrangement of a noncyclic substrate - some new observations
