A new catalytic mode of the modularly designed organocatalysts (MDOs): Enantioselective synthesis of dihydropyrano[2,3-c]pyrazoles

Tetrahedron Letters

Volumn 52, Issue 30, 2011, Pages 3905-3908

  Muramulla, Savitha ^a   Zhao, Cong Gui ^a  

^a UNIVERSITY OF TEXAS AT SAN ANTONIO   (United States)

Author keywords

Cinchona alkaloid; Modularly designed organocatalyst; Organocatalysis; Pyrano 2,3 c pyrazole; Tandem reaction

Indexed keywords

CINCHONA ALKALOID; LEWIS BASE; NUCLEOPHILE; PYRAZOLE DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIZATION; ENANTIOSELECTIVITY; MICHAEL ADDITION; MODULARLY DESIGNED ORGANOCATALYST; SYNTHESIS;

CINCHONA;

EID: 79959520911     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.05.092     Document Type: Article

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27. General procedure: In a vial equipped with a magnetic stirring bar were added quinidine thiourea (11, 5.0 mol %), l-proline (1, 5.0 mol %), 3-methyl-2-pyrazolon-5-one (16, 0.10 mmol) and finally benzylidenemalononitrile (17a, 0.10 mmol) in dichloromethane (2.0 mL) with stirring. The mixture was further stirred at room temperature until the completion of the reaction (monitored by TLC). The reaction mixture was directly transferred to a silica gel column and was purified by column chromatography (with EtOAc as the eluent) to furnish the desired product.