Efficient Synthesis of Chiral Propargyl Alcohols by Enantioselective Titanium-TADDOLate Catalyzed Addition of Dimethylzinc to 3-Trimethylsilyl-2-propynal
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Abstract:
A practical and efficient synthesis of chiral propargyl alcohols was achieved by the enantioselective addition of dimethylzinc to 3-trimethylsilyl (TMS)-2-propynal (5) using titanium-TADDOLate (α,α,α’,α’-tetraaryl-2,2-disubstituted-1,3-dioxolane-4,5-dimethanolate) catalysts.Keywords:
Dimethylzinc
Propargyl
Trimethylsilyl
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Propargyl
Dimethylzinc
Trimethylsilyl
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This chapter contains sections titled: Summary Introduction Early Studies Rh(I)-Catalyzed Enantioselective Hydroarylation of Iminoarenes Pt(II)-Catalyzed Enantioselective Hydroarylation of Alkenylindoles Au(I)-Catalyzed Enantioselective Hydroarylation of Allenylindoles Conclusions and Outlook Experimental: Selected Procedures References
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Domino
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Mannich reaction
Aldol reaction
Hydrocyanation
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Abstract The development of efficient CO 2 utilization reactions has gained a significant amount of attention in recent years. Although transformations of CO 2 to produce basic chemicals have been extensively investigated, the development of catalytic enantioselective CO 2 utilization reactions for the preparation of fine chemicals remains limited at this stage. Several excellent methods for catalytic enantioselective CO 2 utilization using chiral metal complex catalysts have been reported. Many researchers have also focused on developing organocatalyzed approaches to enantioselective CO 2 utilization, and several excellent examples have appeared in recent years. Herein, recent advances in catalytic enantioselective CO 2 utilization reactions using chiral organocatalysts are reviewed to provide a forecast for organocatalyzed enantioselective CO 2 utilization research.
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The first catalytic enantioselective route to (R)-(+) Lasiodiplodin is described. Introduction of the asymmetric center was accomplished by the enantioselective addition of dimethyl zinc to an aldehyde, mediated by a tricarbonyl (η6 arene) chromium(0) catalyst.
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A comparison of different titanium catalysts in the enantioselective opening of meso-epoxides has been carried out. The best catalyst is readily available in both enantiomers from menthol and allows for a highly enantioselective reaction.
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Abstract It is proposed that asymmetric syntheses be divided into enantioselective and diastereoselective syntheses. The enantioselective hydrogenations discussed in the present progress report were catalyzed by Raney nickel that had previously been treated with solutions of optically active compounds. Relationships exist between the enantioselectivity of the catalyst and the structure of the chiral compound used to modify it.
Raney nickel
Asymmetric hydrogenation
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This review focuses on the enantioselective synthesis of halogenated molecules having a chiral halocarbon center. In particular, this review discusses enantioselective transformations with haloalkenes and enantioselective α-substitutions of α-halo carbonyl compounds. Enantioselective halogen-transfer reactions are excluded from this review.
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This chapter contains sections titled: Introduction and Extent of This Chapter Propargyl Esters Propargyl Ethers Propargyl Alcohols Propargyl Amines Propargyl Carbonates, Amides, and Carbamates Other Propargyl Substitution Patterns Conclusion References
Propargyl
Propargyl alcohol
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