The alkylation of the chiral Schiff base derived from the condensation of (+)-ketopinic acid and diethyl aminomethylphosphonate followed by hydrolysis affords diethyl (S)-alpha-amino-alpha-alkyl phosphonates with high enantiomeric excesses when benzyl or allyl halides are used in the alkylation step. An improved procedure for the preparation of diethyl aminomethylphosphonate is also reported.
ASYMMETRIC-SYNTHESIS OF DIETHYL ALPHA-AMINO-ALPHA-ALKYL-PHOSPHONATES BY ALKYLATION OF THE CHIRAL SCHIFF-BASE DERIVED FROM (+)-KETOPINIC ACID AND DIETHYLAMINOMETHYL PHOSPHONATE / M. FERRARI, G. JOMMI, G. MIGLIERINI, R. PAGLIARIN, M. SISTI. - In: SYNTHETIC COMMUNICATIONS. - ISSN 0039-7911. - 22:1(1992), pp. 107-123.
ASYMMETRIC-SYNTHESIS OF DIETHYL ALPHA-AMINO-ALPHA-ALKYL-PHOSPHONATES BY ALKYLATION OF THE CHIRAL SCHIFF-BASE DERIVED FROM (+)-KETOPINIC ACID AND DIETHYLAMINOMETHYL PHOSPHONATE
R. PAGLIARIN;
1992
Abstract
The alkylation of the chiral Schiff base derived from the condensation of (+)-ketopinic acid and diethyl aminomethylphosphonate followed by hydrolysis affords diethyl (S)-alpha-amino-alpha-alkyl phosphonates with high enantiomeric excesses when benzyl or allyl halides are used in the alkylation step. An improved procedure for the preparation of diethyl aminomethylphosphonate is also reported.Pubblicazioni consigliate
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