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Synthesis of α-amino phosphonic acids via oxoiminium salts

✍ Scribed by Shatzmiller, Shimon ;Dolitzky, Ben-Zion ;Meirovich, Revital ;Neidlein, Richard ;Weik, Christian

Publisher: John Wiley and Sons
Year: 1991
Tongue: English
Weight: 463 KB
Volume: 1991
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199119910129

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The oxoiminium salts 4a, b, and 8 obtained by alkylation with Et~3~OBF~4~ of the aldonitrones 3a, b, and 7 react with diphenyl hydrogen phosphite to give the N‐alkoxy α‐amino phosphonic esters 6 and 9a, b. Similarly, the cyclic imine oxides 10a, b and the cyclic oxime ethers 14a, b afford the α‐branched N‐alkoxy α‐amino phosphonic esters 12a, b and 16a, b, respectively. Hydrogenolysis and ester hydrolysis affords the α‐methyl α‐amino phosphonic acid hydrochlorides 13a, b and 17a, b.

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