Diethyl alpha-amino-alpha-alkyl-phosphonates are obtained in good to high enantiomeric excesses by alkylation of chiral phosphonoglycine equivalents embodying the camphor skeleton. The chelating effects in the alkylation step play an important role in enhancing the diastereoselectivity of the reaction as substantiated by semiempirical calculations (AM1).
Asymmetric synthesis of diethyl α-amino- α-alkyl-phosphonates by alkylation of chiral phosphonoglycine equivalents: role of chelating effects / G. Jommi, G. Miglierini, R. Pagliarin, G. Sello, M. Sisti. - In: TETRAHEDRON-ASYMMETRY. - ISSN 0957-4166. - 3:9(1992), pp. 1131-1134. [10.1016/S0957-4166(00)82094-7]
Asymmetric synthesis of diethyl α-amino- α-alkyl-phosphonates by alkylation of chiral phosphonoglycine equivalents: role of chelating effects
R. Pagliarin;G. SelloPenultimo
;
1992
Abstract
Diethyl alpha-amino-alpha-alkyl-phosphonates are obtained in good to high enantiomeric excesses by alkylation of chiral phosphonoglycine equivalents embodying the camphor skeleton. The chelating effects in the alkylation step play an important role in enhancing the diastereoselectivity of the reaction as substantiated by semiempirical calculations (AM1).
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