Protonation of acyl anion equivalents generated from acylphosphonates: nonhydride access to the aldehyde oxidation state from the carboxylic acid oxidation state

Acylphosphonates, which are easily available from carboxylic acids, are potent acyl anion precursors and undergo cyanide ion promoted phosphonate–phosphate rearrangement to provide the corresponding acyl anion equivalents as reactive intermediates. The protonation of these acyl anion equivalents fur...

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Bibliographic Details
Published in:Tetrahedron 2007, Vol.63 (1), p.160-165
Main Authors: Demir, Ayhan S., Reis, Ömer, Esiringü, Ilker, Reis, Barbaros, Baris, Sehriban
Format: Article
Language:English
Subjects:
Acyl anion
Acylphosphonates
Carboxylic acids
Cyanohydrin O-phosphates
Rearrangements
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Summary:Acylphosphonates, which are easily available from carboxylic acids, are potent acyl anion precursors and undergo cyanide ion promoted phosphonate–phosphate rearrangement to provide the corresponding acyl anion equivalents as reactive intermediates. The protonation of these acyl anion equivalents furnished cyanohydrin O-phosphates in good yields. For the high yield formation of cyanohydrin O-phosphates from arylphosphonates THF should be used and from alkylphosphonates DME was used. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2006.10.036