Journal
ORGANIC LETTERS
Volume 10, Issue 18, Pages 3981-3984Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol801463g
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- Ministerio de Educacion, Cultura y Deporte [CTQ2005-01792]
- Ministerio de Ciencia y Tecnologia
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Deprotonation of bis(N-benzyl-N-methyl)-P-arylphosphonic diamides with s-BuLi in THF at -90 degrees C takes place selectively at the benzylic position. The anions undergo intramolecular attack to the P-aryl ring leading to dearomatized species that were trapped with a series of electrophiles (MeOH, ArOH, BnBr, aliphatic and aromatic aldehydes, and benzophenone) in very high yield, and with high regio- and stereocontrol. The dearomatized products were smoothly transformed into gamma-aminophosphonic acids under acidic conditions. Preliminary screening for antitumor activity showed promising levels of activity.
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