Lewis Acid Catalyzed Synthesis of N-Protected Diphenyl 1-Aminoalkyl­phosphonates

Pieter Van der Veken; Ibrahim El Sayed; Jurgen Joossens; Christian V. Stevens; Koen Augustyns; Achiel Haemers

doi:10.1055/s-2004-837307

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Lewis Acid Catalyzed Synthesis of N-Protected Diphenyl 1-Aminoalkylphosphonates

Pieter Van der Veken^a, Ibrahim El Sayed^a, Jurgen Joossens^a, Christian V. Stevens^b, Koen Augustyns^a, Achiel Haemers*^a
^a Department of Medicinal Chemistry, , University of Antwerp, Universiteitsplein 1, 2610 Antwerp, Belgium
Fax: +32(3)8202739; e-Mail: achiel.haemers@ua.ac.be;
^b Department of Organic Chemistry, Faculty of Agricultural and Applied Biological Sciences, Ghent University, Coupure links 653, 9000 Ghent, Belgium

Abstract

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Abstract

Diphenyl α-aminomethylphosphonates are prepared in good yields using a Lewis acid catalyzed Birum-Oleksyszyn reaction. This approach enlarges the scope of this reaction, allowing the use of aldehydes and ketones and the use of acid-labile groups in the synthesis of mono-and disubstituted diphenyl 1-aminoalkylphosphonates.

Key words

diphenyl 1-aminoalkylphosphonates - carbamates - Lewis acid - aldehydes - ketones

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References

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Lewis Acid Catalyzed Synthesis of N-Protected Diphenyl 1-Aminoalkyl­phosphonates

Lewis Acid Catalyzed Synthesis of N-Protected Diphenyl 1-Aminoalkylphosphonates