Download PDF by Eric N Jacobsen: Comprehensive asymmetric catalysis [...] CD-ROM

By Eric N Jacobsen

ISBN-10: 3540146954

ISBN-13: 9783540146957

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Described hetero Diels-Alder reactions of aldehydes and activated dienes catalyzed by the lanthanide catalyst Eu(hfc)3 which gave a moderate enantioselectivity (58% ee) [73]. [74] and Reetz et al. [75] used catalytic amounts of (RO)2TiCl2 (binolate or taddolate respectively) in the Diels-Alder reaction of cyclopentadiene with some simple dienophiles. Narasaka et al. reached an enantioselectivity close to 90%. Kauffman et al. [76] found in 1987 that a chiral boron reagent RBBr2 (R= pinanyl) was a catalyst for the Diels-Alder reaction, giving a modest ee.

This article will only describe the generation of stereogenic centers and leave the synthesis of facially or axially chiral molecules to other review articles [2]. If the substrate is achiral, asymmetric synthesis will generate one out of two enantiomers (enantioselective synthesis). If the substrate already contains other stereogenic units, or if the reaction generates more than one stereogenic center in one act in an achiral substrate, the asymmetric synthesis creates one out of several possible diastereomers (diastereoselective synthesis).

In reaction (28) (Scheme 11) the substrate adopts an extended conformation, whereas in reaction (29) (Scheme 11) the A1,3-strain effect is operative [29]. In cyclic hydroxysufoximides, which are obtained by the addition of the corresponding sulfoximine carbanion to the cyclic ketone, the cyclopropanation is again directed syn to the OH-group. After the addition the sulfoximine is eliminated by thermolysis [reaction (30), Scheme 11] [30]. Homogeneous catalytic hydrogenations can also be performed under the directing effect of free hydroxy functions (Scheme 12).

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