Enantioselective Construction of 2-Aryl-2,3-dihydrobenzofuran Scaffolds Using Cu/SPDO-Catalyzed [3 + 2] Cycloaddition
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A new, efficient approach toward the preparation of 2-aryl-2,3-dihydrobenzofuran scaffolds through the Cu/SPDO-catalyzed [3 + 2] cycloaddition between quinone ester and styrene derivatives has been developed. The procedure features excellent enantioselectivities (up to 99% ee), high yields (up to 96%), and broad substrate tolerance. Additionally, asymmetric synthesis of natural corsifurans A and B from commercially available starting materials has also been achieved in two or three steps using this reaction as a key transformation.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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The enantioselective N-heterocyclic carbene-catalysed formal 2+2- and 2+2+2- cycloadditions of ketenes with isothiocyanates can be investigated. At room temperature, the reaction of N-arylthiocyanates favours the 2+2-cycloaddition. However, at −40°C, N-benzoylisothiocyanates undergo the 2+2+2-cycloaddition. This chapter discusses cycloaddition-type addition reactions. Specifically, it covers three types of cycloadditions: 2+2-cycloaddition, 2+3-cycloaddition and 2+4-cycloaddition. Miscellaneous cycloaddition reactions are separately described at the end of the chapter.
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Mannich reaction
Aldol reaction
Hydrocyanation
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Enantioselective biomimetic polyene cyclizations of polyprenoids have been studied for a long time. Very recently, we have developed the first iodonium ion-induced enantioselective polyene cyclization of polyprenoids using a nucleophilic promoter. Achiral nucleophilic phosphorus compounds catalytically promote the diastereoselective halocyclization in dichloromethane to give a halogenated cyclic product in excellent yield. Moreover, chiral phosphoramidites stoichiometrically promote the enantioselective halocyclization of simple polyprenoids with N-iodosuccinimide in toluene to give iodinated cyclic products in up to 99 percent ee and 99 percent ds. Some enantioselective polycyclizations have been reported in addition to this halocyclization. One of the advantages of these biomimetic polycyclizations is the simultaneous formation of several carbon-carbon bonds with the relative and absolute stereocontrol. Enantioselective biomimetic domino reactions would be highly useful for the practical synthesis of natural products and related compounds.
Polyene
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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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