- A convenient method for the preparation of chiral phosphonoacetamides and their Horner-Wadsworth-Emmons reaction
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Chiral phosphonoacetamides bearing (S)-(α-methylbenzyl)benzylamine, (S,S)-bis(α-methylbenzyl)amine, l-phenylglycine methyl ester and l-phenylglycinol were easily prepared in good yield by means of the Michaelis-Arbuzov reaction of chiral bromoacetamides obtained in quantitative yield, with trimethyl phosphite, which under Horner-Wadsworth-Emmons conditions with several aryl and alkyl aldehydes under Masamune-Roush procedure using LiCl and DBU in THF or toluene gave the corresponding chiral α,β-unsaturated amides. The present procedure is a convenient and efficient methodology for the preparation of phosphonoacetamides and chiral α,β-unsaturated amides in high E-selectivity.
- Ordonez, Mario,Hernandez-Fernandez, Eugenio,Montiel-Perez, Martin,Bautista, Rafael,Bustos, Paola,Rojas-Cabrera, Haydee,Fernandez-Zertuche, Mario,Garcia-Barradas, Oscar
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p. 2427 - 2436
(2008/03/13)
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