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

Tetrahedron Letters

Volumn 50, Issue 8, 2009, Pages 876-879

  Powell, Magdalena E ^a   Kelly, Andrew M ^a   Bull, Steven D ^a   James, Tony D ^a  

^a University of Bath Claverton Down   (United Kingdom)

Author keywords

1,2 Amino alcohol; 1H NMR spectroscopy; Boronate esters; Chiral derivatisation agent; Enantiomeric excess

Indexed keywords

AMINOALCOHOL; BORONIC ACID DERIVATIVE; O SILYL 1,2 AMINOALCOHOL; PHENYLPROPIONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DERIVATIZATION; ENANTIOMER; ENANTIOSELECTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM;

EID: 58149334774     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.12.013     Document Type: Article

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44. 1H NMR derivatisation protocols were BINOL, (syn)-methyl 2,3-dihydroxy-3-phenylpropionate, dimethyltartrate, dibenzyltartrate, phenyl-ethane-1,2-diol, 2-phenyl-1,2-propanediol, 3,3-dimethyl-1,2-butanediol, 1,2-propanediol, 1,3-butanediol and 2,3-pinanediol.
45. Enantiopure O-silyl-amino alcohols 12a-j and (rac)-syn-diol 13 were used for experimental simplicity because it enabled a single stock solution of (rac)-13 to be used for derivatisation.
46. For a detailed experimental account of how to determine enantiomeric excess using this derivatisation technique see Ref. 12d.