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. 2004 Apr 20;101(16):5723-6.
doi: 10.1073/pnas.0307152101. Epub 2004 Apr 6.

Design of chiral ligands for asymmetric catalysis: from C2-symmetric P,P- and N,N-ligands to sterically and electronically nonsymmetrical P,N-ligands

Andreas Pfaltz  1 , William J Drury 3rd
Affiliations

Design of chiral ligands for asymmetric catalysis: from C2-symmetric P,P- and N,N-ligands to sterically and electronically nonsymmetrical P,N-ligands

Andreas Pfaltz et al. Proc Natl Acad Sci U S A. .

Abstract

For a long time, C(2)-symmetric ligands have dominated in asymmetric catalysis. More recently, nonsymmetrical modular P,N-ligands have been introduced. These ligands have been applied successfully in various metal-catalyzed reactions and, in many cases, have outperformed P,P- or N,N-ligands.

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Figures

Fig. 1.
Fig. 1.
Privileged ligand structures.
Fig. 2.
Fig. 2.
Kagan's DIOP and Knowles' DiPAMP ligands.
Fig. 3.
Fig. 3.
Structure of a semicorrin metal complex.
Fig. 4.
Fig. 4.
Achiwa's hydrogenation studies with desymmetrized DIOP.
Fig. 5.
Fig. 5.
Industrial process for the production of (S)-metolachlor.
Fig. 6.
Fig. 6.
Structure of PHOX ligands and x-ray data of an allyl–Pd complex.
Fig. 7.
Fig. 7.
Mechanism of enantioselective Pdcatalyzed allylic substitution.
Fig. 8.
Fig. 8.
Modular construction of PHOX ligands 1.
Fig. 9.
Fig. 9.
Ligand optimization for regioselective and enantioselective allylic substitution.
Fig. 10.
Fig. 10.
Ir-catalyzed asymmetric hydrogenation of olefins.
See this image and copyright information in PMC

References

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    1. Ohkuma, T., Kitamura, M. & Noyori, R. (2000) in Catalytic Asymmetric Synthesis, ed. Ojima, I. (Wiley–VCH, New York), 2nd Ed., pp. 1–110.
    1. Pfaltz, A. & Lautens, M. (1999) in Comprehensive Asymmetric Catalysis, eds. Jacobsen, E. N., Pfaltz, A. & Yamamoto, H. (Springer, Berlin), Vol. 2, pp. 833–884.
    1. Trost, B. M. & Lee, C. (2000) in Catalytic Asymmetric Synthesis, ed. Ojima, I. (Wiley–VCH, New York), 2nd Ed., pp. 593–649.
    1. Yoon, P. Y. & Jacobsen, E. N. (2003) Science 299, 1691–1693. - PubMed

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