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


Reference:

Powell, M. E., Kelly, A. M., Bull, S. D. and James, T. D., 2009. A simple chiral derivatisation protocol for H-1 NMR spectroscopic analysis of the enantiopurity of O-silyl-1,2-amino alcohols. Tetrahedron Letters, 50 (8), pp. 876-879.

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http://dx.doi.org/10.1016/j.tetlet.2008.12.013

Abstract

A simple chiral derivatisation protocol for determining the enantiopurity of O-silyl-protected-1,2-amino alcohols by H-1 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.

Details

Item Type Articles
CreatorsPowell, M. E., Kelly, A. M., Bull, S. D. and James, T. D.
DOI10.1016/j.tetlet.2008.12.013
Uncontrolled Keywords2-amino alcohol, 1, chiral derivatisation agent, h-1 nmr spectroscopy, enantiomeric excess, boronate esters
DepartmentsFaculty of Science > Chemistry
RefereedYes
StatusPublished
ID Code13455

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