A simple chiral derivatisation protocol for 1H NMR spectroscopic analysis of the enantiopurity of O-silyl-1,2-amino alcohols

A simple chiral derivatisation protocol for determining the enantiopurity of O-silyl-protected-1,2-amino alcohols by 1H NMR spectroscopic analysis is described, which involves their treatment with 2-formylphenylboronic acid and enantiopure ( syn)-methyl-2,3-dihydroxy-3-phenylpropionate to afford mix...

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Bibliographic Details
Published in:Tetrahedron letters 2009-02, Vol.50 (8), p.876-879
Main Authors: Powell, Magdalena E., Kelly, Andrew M., Bull, Steven D., James, Tony D.
Format: Article
Language:English
Subjects:
1,2-Amino alcohol
1H NMR spectroscopy
Boronate esters
Chiral derivatisation agent
Enantiomeric excess
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Summary:A simple chiral derivatisation protocol for determining the enantiopurity of O-silyl-protected-1,2-amino alcohols by 1H NMR spectroscopic analysis is described, which involves their treatment with 2-formylphenylboronic acid and enantiopure ( syn)-methyl-2,3-dihydroxy-3-phenylpropionate to afford mixtures of imino-boronate esters whose diastereoisomeric ratio is an accurate reflection of the enantiopurity of the parent amino alcohol.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2008.12.013