ISSN 1017-2548(Print)
ISSN 2234-8530(Online)
Volume 39, Number 10
JKCSEZ 39(10)
August 20, 1995 

Mukaiyama reaction of silyl nucleophiles with phosphonoaldehydes was developed. In order to find the optimum condition, various Lewis acid, solvent were examined by taking the reaction of diethyl phosphonoacetaldehyde with silyl enol ether of acetophenone as a model and finally BF3·OEt2 in dichloromethane was found to be an excellent catalyst. This method was proved to be a good method to synthesize the hydroxyphosphonate derivatives via reaction of various silyl enol ether with phosphonoacetaldehyde. Previously unreported compounds were synthesized. They are diethyl 4-oxo-2-hydroxy-2-phenylbutylphosphonate, diethyl 4-oxo-2-hydroxy-4-methoxybutylphosphonate, diethyl 2-hydroxypent-4-enylphosphonate, diethyl 2,2-trimethylsiloxycyanoethylphosphonate, diethyl 2-hydroxy-2-(2-oxocyclohexyl)ethylphosphonate, diethyl 3-hydroxy-3-(2-oxocyclohexyl)propylphosphonate. All the compounds prepared in this study were identified by means of 1H NMR spectroscopy, IR spectroscopy and GC/MS spectrometry.