Electro Chemistry For Organic Compounds
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Extra resources for Electro Chemistry For Organic Compounds
71). The crucial finding was that the absence of molecular sieves is essential for high enantioselectivity, whereas their presence is necessary for the formation of the chiral titanium catalyst from BINOL and TiCl2(O-i-Pr)2. In the presence of molecular sieves, however, the DielsAlder cycloadduct was obtained in only 9% ee. The molecular sieves-free BINOLTiCl2(O-i-Pr)2 complex, which was prepared by centrifugation of the suspension and decanting, gave cycloadducts in high optical purity which are useful chiral building blocks for the synthesis of anthracyclines and tetracyclines.
A. Evans, J. S. Johnson, Diels-Alder Reaction, in: Comprehensive Asymmetric Catalysis, Vol. III, E. N. Jacobsen, A. Pfaltz, H. Yamamoto (Eds), Springer, New York, 1999, p 1177; (b) H. B. Kagan, O. Riant, Chem. Rev. 1992, 92, 1007; (c) K. Narasaka, Synthesis 1991, 1; (d) K. Maruoka, H. Yamamoto, Asymmetric Reactions with Chiral Lewis Acid Cata- lysts, in: Catalytic Asymmetric Synthesis, I. ), VCH, New York, 1993, p 413; (e) R. Noyori, Asymmetric Catalysis, in: Organic Synthesis, John Wiley and Sons, New York, 1994, p 212.
Another noteworthy feature of the titanium catalyst 10 is that the enantioselectivity is not greatly influenced by reaction temperature (96% ee at –78 8C, 92% ee at –20 8C, 88% ee at 0 8C in the reaction of acrolein and cyclopentadiene). This is unusual for metal-catalyzed asymmetric reactions, with only few similar examples. The titanium catalyst 10 acts as a suitable chiral template for the conformational fixing of a,b-unsaturated aldehydes, thereby enabling efficient enantioface recognition, irrespective of temperature.