The assignment of the absolute configuration of 1,2-diols by low-temperature NMR of a single MPA derivative

Organic Letters

Volumn 7, Issue 22, 2005, Pages 4855-4858

  Freire, Félix ^a   Seco, José Manuel ^a   Quiñoá, Emilio ^a   Riguera, Ricardo ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALPHA METHOXY ALPHA PHENYLACETIC ACID; ALPHA-METHOXY-ALPHA-PHENYLACETIC ACID; ESTER; PHENYLACETIC ACID DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

ALCOHOLS; ESTERS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PHENYLACETATES; STEREOISOMERISM;

EID: 27644450535     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol051764s     Document Type: Article

References (24)

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20. 2).
21. The pro-(R)- and pro-(S)-methylene protons have been assigned by means of deuteration experiments.
22. Note that in a type A diol the pro-(R)-methylene proton resonates at high field and the pro-(S) resonates at low field, while in a type B diol the opposite situation applies. For simplification purposes, we will refer to them as high- and low-field protons.
23. 2 is a very convenient NMR solvent for these experiments.
24. T1T2 value to safely distinguish types A and B is 0.07 ppm and at 240 K is 0.04 ppm.