A mild and efficient synthesis of α-tosylamino ketones from aryl aziridines in the presence of β-cyclodextrin and NBS in water

Tetrahedron Letters

Volumn 46, Issue 8, 2005, Pages 1299-1301

  Reddy, M Somi ^a   Narender, M ^a   Rao, K Rama ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Amino ketones; Cyclodextrin; Aziridines; Water

Indexed keywords

AZIRIDINE; BETA CYCLODEXTRIN; KETONE;

ANALYTIC METHOD; ARTICLE; COMPLEX FORMATION; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 13244252375     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.12.125     Document Type: Article

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21. General procedure: β-Cyclodextrin (1 mmol) was dissolved in water (15 ml) at 60°C, and the aziridine (1 mmol) dissolved in acetone (2 ml) was added slowly with stirring. After 15 min, NBS (1.0 mmol) was added and the mixture stirred for 12 h at 50°C. The organic material was extracted with ethyl acetate. The organic phase was separated, filtered, and washed with brine then dried over sodium sulfate and the solvent removed under vacuum. The crude product was purified by column chromatography with ethyl acetate:hexane (20:80) as eluent. The aqueous layer was cooled to 5°C to recover precipitated CD by filtration. The filtrate which contained succinimide was evaporated and the residue purified and converted to NBS
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