Regioselective ring-opening of aziridines with potassium thiocyanate in the presence of β-cyclodextrin in water

Tetrahedron Letters

Volumn 46, Issue 38, 2005, Pages 6437-6439

  Somi Reddy, M ^a   Narender, M ^a   Nageswar, Y V D ^a   Rama Rao, K ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Aminothiocyanates; Cyclodextrin; Aziridines; Biomimetic; Potassium thiocyanate; Water

Indexed keywords

AZIRIDINE DERIVATIVE; BETA CYCLODEXTRIN; THIOCYANATE POTASSIUM; WATER;

ARTICLE; REACTION ANALYSIS; RING OPENING; ROOM TEMPERATURE;

EID: 23844520780     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.114     Document Type: Article

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35. General procedure: To a solution of β-cyclodextrin (1 mmol) dissolved in distilled water (15 ml) at 60°C, aziridine (1 or 3 ) (1 mmol) dissolved in acetone (2 ml) was added slowly with stirring. The mixture was cooled to room temperature, KSCN (2 mmol) was added then the reaction mixture was stirred at room temperature for 26 h and the product was extracted with ethyl acetate (3 x 50 ml). The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product thus obtained was purified by column chromatography on silica gel (60-120 mesh) using ethyl acetate/hexane (85:15) as eluent.
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