Unusual reductive cleavage of 3-aryl-2,3-epoxyamides by using samarium diiodide. Synthesis of 3-aryl-3-deuterio-2-hydroxyamides with total regioselectivity

Tetrahedron Letters

Volumn 44, Issue 28, 2003, Pages 5323-5326

  Concellón, José M ^a   Bardales, Eva ^a   Gómez, Cecilia ^b  

^a UNIVERSITY OF OVIEDO   (Spain)

^b UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 EPOXYAMIDE; ALDEHYDE DERIVATIVE; AMIDE; DEUTERIUM OXIDE; KETONE DERIVATIVE; LITHIUM; POTASSIUM DERIVATIVE; SAMARIUM DIIODIDE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COLUMN CHROMATOGRAPHY; ENANTIOMER; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

EID: 0038007833     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01201-2     Document Type: Article

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29. 4), filtered, and concentrated in vacuo to afford crude 3-aryl-2-hydroxyamides or 3-aryl-3-deuterio-2-hydroxyamides 2, which were purified by flash column chromatography on silica gel (hexane/AcOEt 3:1) or vacuum distillation (see Table 1).
30. In the case of aromatic tetrasubstituted α,β-epoxyamides, the reaction was carried out at -25°C during 3.5 h.
31. + of the corresponding undeuterated compounds, indicating a presence of the no deuterated compound <1%.
32. 2O (0.4 mL) in THF (24 mL) was added under a nitrogen atmosphere, to a stirred solution of 3 (0.4 mmol) in THF (2 mL) at -25°C. The mixture was stirred for 2.5 h at this temperature and then quenched with aqueous HCl (0.1 M, 15 mL). The same workup used for isolated compounds 2 afforded crude 2-deuterio-3-hydroxyamides 4, which were purified by flash column chromatography on silica gel (hexane/AcOEt, 3:1).
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