Synfacts 2011(3): 0344-0344  
DOI: 10.1055/s-0030-1259461
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Domino Reaction with Ionic Liquid Immobilized Prolinol Derivatives

Contributor(s): Yasuhiro Uozumi, Haifeng Zhou
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
Further Information

Publication History

Publication Date:
16 February 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)].