Aza-Michael reactions with vinyl sulfones and Amberlyst-15 as catalyst

Tetrahedron Letters

Volumn 48, Issue 51, 2007, Pages 9040-9043

  Esteves, Ana P ^a   Silva, Marília E ^a   Rodrigues, Lígia M ^a   Oliveira Campos, Ana M F ^a   Hrdina, Radim ^b  

^a UNIVERSITY OF MINHO   (Portugal)

^b UNIVERSITY OF PARDUBICE   (Czech Republic)

Author keywords

Amberlyst 15; Aza Michael; Nitrogen nucleophiles; Vinyl sulfones

Indexed keywords

4 AMINOPHENYLVINYLSULFONE; AMINE; METHYL VINYL SULFONE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONJUGATION; MICHAEL ADDITION; NUCLEAR MAGNETIC RESONANCE;

EID: 36249014848     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.077     Document Type: Article

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14. Typical experimental procedure: To a mixture of vinyl sulfone (2.5 mmol) and Amberlyst-15 (30% w/w), the amine (2 mmol) was added and stirred at room temperature for the appropriate time (Table 1). The reaction was followed by TLC. The final mixture was diluted with dichloromethane (10 mL) and the catalyst removed by filtration. The solvent was evaporated and the crude residue afforded the pure compounds in some cases (Table 1). Some of the residues were purified by column chromatography or preparative layer chromatography using as eluent typically mixtures of chloroform-methanol or ethyl acetate-light petroleum.
15. 3) 23.41 (C-2″ and C-3″), 49.08 (C-2′), 53.82 (C-1″ and C-4″), 55.33 (C-1′), 113.98 (C-2 and C-6), 127.00 (C-4), 130.08 (C-3 and C-5), 151.50 (C-1) ppm; HRMS (FAB) m/z 255.1169 (100%).