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Synfacts 2011(4): 0407-0407  
DOI: 10.1055/s-0030-1259651
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Cinchona-Derived Amino Phosphine Precatalysts for Cooperative Catalysis

Contributor(s): Mark Lautens, Norman Nicolaus
F. Sladojevich, A. Trabocchi, A. Guarna, D. J. Dixon*
University of Oxford, UK and Università di Firenze, Sesto Fiorentino, Italy
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Publikationsdatum:
18. März 2011 (online)

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Significance

Cooperative catalysis in combination with transition-metal ions to achieve asymmetric induction is an emerging research area. Herein, the authors describe a new class of chiral amino phosphine precatalysts of type 4 and 5 derived from cinchona alkaloids. It was found that these precatalysts could be used in combination with silver(I) salts to perform the asymmetric aldol reaction between isocyanates 1 and aldehydes 2. The formed oxazolines of type 3 could be obtained in high yields and with excellent diastereo- and enantioselectivities.