Stereocontrolled synthesis of hydroxyethylamine isosteres via chiral sulfoxide chemistry

Tetrahedron Letters

Volumn 45, Issue 26, 2004, Pages 5125-5129

  Pesenti, Cristina ^a   Arnone, Alberto ^a   Arosio, Paolo ^a   Frigerio, Massimo ^a   Meille, Stefano V ^a   Panzeri, Walter ^a   Viani, Fiorenza ^a   Zanda, Matteo ^a  

^a CNR   (Italy)

Author keywords

Mannich reaction; Peptidomimetics; Sulfoxides

Indexed keywords

DIAMINE; DIPEPTIDE DERIVATIVE; ETHYLAMINE; HYDROXYETHYLAMINE DIPEPTIDE ISOSTERE; OXAZOLIDINONE DERIVATIVE; SAQUINAVIR; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; DRUG SYNTHESIS; EPIMER; ISOSTERE; LITHIATION; QUANTUM YIELD; STEREOCHEMISTRY;

EID: 2942564312     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.04.160     Document Type: Article

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27. 4Cl solution was added, the organics were extracted with AcOEt (3 × 30 mL), the combined extracts were dried over anhydrous sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The crude was purified by flash chromatography (FC) affording the products 2
28. S)-stereochemistry
29. 1H NMR stereochemical assignments will be published in a full paper
30. 4Cl solution was then added, the resulting mixture was diluted with water and the organics were extracted with ethyl acetate (3 × 50 mL), dried over anhydrous sodium sulfate, filtered and the solvent evaporated at reduced pressure to give a residue, that was purified by FC
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