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• W2950317874 abstract "The notion of internal (or intramolecular) cooperativity of chirality is reviewed on the basis of various examples of diastereoisomeric ferrocenylphosphine ligands used in the gold(I)-catalyzed aldol reaction. It was found that the stereochemical outcome of this reaction strongly depends on the specific combination of the absolute configuration of the different stereogenic centers present in the ligand. Thus, individual chirotopic segments in these ligand molecules can act either in a cooperative or noncooperative manner in determining both diastereo-and enantioselectivity. Furthermore, several examples of application of the strategy of double stereodifferentiation (external, or intermolecular cooperativity of chirality) in the gold(I)-catalyzed aldol reaction and the vanadium(IV)-catalyzed hetero Diels–Alder condensation are presented. Based on our work it is apparent that, whether the diastereoselectivity of these two reactions is controlled by the catalyst or by a chiral substrate, cannot be predicted and very much depends on the nature of every individual reactant. Thus, it was found that in both reactions the chiral aldehyde substrate usually has a strong impact on the diastereoselectivity, leading to interesting patterns of double asymmetric induction. On the other hand, chiral isocyanoacetate and chiral-activated dienes, respectively, showed little or no effect on the stereochemical outcome of the reactions." @default.
• W2950317874 created "2019-06-27" @default.
• W2950317874 creator A5039255382 @default.
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• W2950317874 date "1991-01-01" @default.
• W2950317874 modified "2023-10-01" @default.
• W2950317874 title "Cooperativity of chirality in homogeneous catalysis: The gold(I)-catalyzed aldol reaction and the vanadium(IV)-catalyzed hetero Diels-Alder cycloaddition" @default.
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• W2950317874 doi "https://doi.org/10.1002/chir.530030419" @default.
• W2950317874 hasPublicationYear "1991" @default.
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