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Synfacts 2011(3): 0344-0344
DOI: 10.1055/s-0030-1259461
DOI: 10.1055/s-0030-1259461
Polymer-Supported Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Domino Reaction with Ionic Liquid Immobilized Prolinol Derivatives
O. V. Maltsev, A. S. Kucherenko, A. L. Chimishkyan, S. G. Zlotin*
N. D. Zelinsky Institute of Organic Chemistry, Moscow and D. I. Mendeleyev University of Chemical Technology of Russia, Moscow, Russian Federation
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
16. Februar 2011 (online)
Significance
An ionic liquid immobilized α,α-diphenylprolinol organocatalyst 3 was developed. The domino reaction of N-protected hydroxylamines 1 and α,α-enals 2 was catalyzed by 3 to give the corresponding 5-hydroxy-3-arylisoxazolidines 4 in up to 94% yield and >99% ee (8 examples). For the formation of 4a, the catalyst was recovered and reused three times [1st use: 99% conversion, 90% ee (major); 4th use: 93% conversion, 90% ee (major)].