Asymmetric Synthesis of Diethyl α-Amino-α-Alkyl-Phosphonates by Alkylation of the Chiral Schiff Base Derived from (+)-Ketopinic Acid and Diethylaminomethyl Phosphonate

Asymmetric Synthesis of Diethyl α-Amino-α-Alkyl-Phosphonates by Alkylation of the Chiral Schiff Base Derived from (+)-Ketopinic Acid and Diethylaminomethyl Phosphonate

The alkylation of the chiral Schiff base derived from the condensation of (+)-ketopinic acid and diethyl aminomethylphosphonate followed by hydrolysis affords diethyl (S)-α-amino-α-alkyl phosphonates with high enantiomeric excesses when benzyl or allyl halides are used in the alkylation step. An imp...

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Veröffentlicht in:Synthetic communications 1992-01, Vol.22 (1), p.107-123
Hauptverfasser: Ferrari, M., Jommi, G., Miglierini, G., Pagliarin, R., Sisti, M.
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container_issue 1
container_start_page 107
container_title Synthetic communications
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creator Ferrari, M.
Jommi, G.
Miglierini, G.
Pagliarin, R.
Sisti, M.
description The alkylation of the chiral Schiff base derived from the condensation of (+)-ketopinic acid and diethyl aminomethylphosphonate followed by hydrolysis affords diethyl (S)-α-amino-α-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.
doi_str_mv 10.1080/00397919208021082
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title Asymmetric Synthesis of Diethyl α-Amino-α-Alkyl-Phosphonates by Alkylation of the Chiral Schiff Base Derived from (+)-Ketopinic Acid and Diethylaminomethyl Phosphonate
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