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Stereoselective synthesis of 1,4,2-oxazaphosphorines as precursors of chiral α-aminophosphonic acids by intramolecular heterocyclization of β-aldiminoalkylphosphites

✍ Scribed by Mudaris N. Dimukhametov; Eugenija V. Bajandina; Elena Yu. Davydova; Igor A. Litvinov; Aidar T. Gubaidullin; Alexey B. Dobrynin; Tatyana A. Zyablikova; Vladimir A. Alfonsov

Publisher: John Wiley and Sons
Year: 2003
Tongue: English
Weight: 110 KB
Volume: 14
Category: Article
ISSN: 1042-7163
DOI: 10.1002/hc.10054

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✦ Synopsis

Abstract

The intramolecular version of nucleophilic additon of phosphites to imines was carried out for the first time taking as an example β‐aldiminoalkylphosphites, formed from chlorophosphites and β‐aldiminoalcohols [N‐(benzylidene)‐2‐aminoethanol and R‐(+)‐N‐(benzylidene)‐2‐aminobutanol‐1]. In these reactions, stereoisomeric 1,4,2‐oxazaphosphorines were obtained in good yields. R‐(+)‐N‐(benzylidene)‐2‐aminobutanol‐1 being used as a precursor, nucleophilic attack by P(III) atom on electrophilic C atom of the CN group proceeds stereospecifically with participation of only re‐face of the two possible diastereotopic faces of the imine double bond to give the epimeric at phosphorus (3R,5R)‐2‐(β‐chloroethyl)‐2‐oxo‐3‐phenyl‐5‐ethyl‐1,4,2‐oxazaphosphorines as precursors of nonracemic α‐aminophosphonic acids. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:56–61, 2003; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.10054

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