Catalytic compositions and methods for asymmetric allylic alkyla

Details Catalytic compositions and methods for asymmetric allylic alkyla Catalytic compositions and methods for asymmetric allylic alkyla

1998-12-15

2000-10-10

Rotman, Alan L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

564167, 546 2, 546341, 540484, 548402, 549206, 549346, 560103, 560104, 560205, C07C 6976, C07C23302, C07F21302, C07F30702, C07D20702

Patent

active

061303496

ABSTRACT:
Complexes of a selected class of chiral ligands with molybdenum, tungsten or chromium, preferably molybdenum, are effective as catalysts in highly enantioselective and regioselective alkylation of allylic substrates. Such compositions provide a versatile and low-cost alternative to existing catalysts.

REFERENCES:
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Agnew. Chem. Int. Ed. Engl. 1995. vol. 34. No. 4, Sep. 1, 1994.
Dvorak, D., et al., "Stereochemistry of Molybdenum (0)-Catalyzed Allylic Substitution: The First Observation of a Syn-Syn Mechanism," J. Am. Chem. Soc. 117:6130-6131 (1995).
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Lloyd-Jones, G.C., and Pfaltz, A., "Chiral Phosphanodihydro-oxazoles in Asymmetric Catalysis: Tungsten-Catalyzed Allylic Substitution," Angew. Chem. Int. Ed. Engl. 34(4) :462-464 (1995).
Rubio, A., and Liebeskind, L.S., "Enantiospecific Synthesis by Transformations of Chiral Pool-Derived Metal .alpha.-Complexes. A Strategy for the Introduction of Substituents on a Pyranose-Derived Lateral .alpha.-Ligand either Syn or Anti to the Coordinating Metal," J. Am. Chem. Soc. 115:891-901 (1993).
Trost, B.M., and Lautens, M., "Chemoselectivity and Stereocontrol in Molybdenum-Catalyzed Allylic Alkylations," J. Am. Chem. Soc. 109:1469-1478 (1987).
Trost, B.M., and Lautens, M., "Regiochemical Diversity in Allylic Alkylations via Molybdenum Catalysts," Tetrahedron 43:21 (4817-4840 (1987).
Trost, B.M., and Merlic, C.A., "Ligand Dependence of Molybdenum-Catalyzed Alkylations. Molybdenum-Isonitrile Complexes as a New Class of Highly Reactive Alkylation Catalysts," J. Am. Chem. Soc. 112:9590-9600 (1990).
Trost, B.M., and Van Vranken, D.L., "Asymmetric Ligands for Transition-Metal-Catalyzed Reactions: 2-Diphenylphosphinobenzoyl Derivatives of C.sub.2 -Symmetric Diols and Diamines," Angew. Chem. Int. Ed. Engl. 31(2) :228-230 (1992).
Trost, B.M., et al., "A Modular Approach for Ligand Design for Asymmetric Allylic Alkylations via Enantioselective Palladium-Catalyzed Ionizations," J. Am. Chem. Soc. 114:9327-9343 (1992).

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