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Enantioselective synthesis of β-hydroxy-α-aminophosphonic acid precursors

✍ Scribed by Antonio Togni; Stephen D. Pastor

Book ID: 104232805
Publisher: Elsevier Science
Year: 1989
Tongue: French
Weight: 154 KB
Volume: 30
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)80362-2

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✦ Synopsis

The gold(I) catalyzed aldol reaction of diethyl a-isocyanomethylphosphonate with benzaldeyde gave the oxazoline 3, a P-hydroxy-a-aminophosphonic acid precursor, with high enantioand diastereoselectivity (98 % tram, 85 % ee) by employing a chiral ferrocenylamine ligand. The use of 31P NMR spectroscopy with the chiral solvating agent (S)-(+)-2,2,2-trifluoro-1-(9-anthryl)ethanol was found to be a powerful tool for determination of optical purity.

The biological activity of a-aminophosphonic acid analogues of the naturally occurring amino acid@

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