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- W2952610081 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 CN 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" @default.
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- W2952610081 date "2003-01-01" @default.
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- W2952610081 title "Stereoselective synthesis of 1,4,2-oxazaphosphorines as precursors of chiral ?-aminophosphonic acids by intramolecular heterocyclization of ?-aldiminoalkylphosphites" @default.
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- W2952610081 doi "https://doi.org/10.1002/hc.10054" @default.
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