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Synthesis 2006(2): 325-331
DOI: 10.1055/s-2005-924768
DOI: 10.1055/s-2005-924768
PAPER
© Georg Thieme Verlag Stuttgart · New YorkDirect Monoalkylation of Alkyl Phosphinates to Access H-Phosphinic Acid Esters
Weitere Informationen
Received
1 July 2005
Publikationsdatum:
21. Dezember 2005 (online)
Publikationsverlauf
Publikationsdatum:
21. Dezember 2005 (online)
Abstract
Simple alkyl phosphinates prepared by the silicate esterification method can be alkylated under Barbier-like conditions with butyl lithium at -78 °C followed by warming to room temperature. The method is limited to the more reactive electrophile such as allylic bromides and alkyl iodides. With these electrophiles good yields of H-phosphinic acid esters are generally obtained in a straightforward manner.
Key words
phosphorus - H-phosphinic acid - phosphinates - alkylation - hypophosphite
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Anilinium hypophosphite is now also commercially available from Aldrich.
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References
The purification of H-phosphinate esters is often complicated by the very polar nature of these compounds, and their relative ease of hydrolysis. Benzyl alkyl-H-phosphinate esters are more labile than other alkyl esters.
14We thank Jakob Heid, Klemens Kaupmann, and Wolfgang Froestl (Novartis Pharma) for conducting the GTPgammaS binding assay.