Reversal of enantioselectivity using catalysts containing multiple stereogenic centres
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Diethylzinc
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Chiral amines are important starting materials for the synthesis of biologically important compounds. Enantioselective addition of dialkylzinc reagents to imines is a reliable method for the synthesis of these compounds. Different chiral catalysts were developed and used for this method. Phosphorous based PFAM catalysts were tried for the first time in the enantioselective synthesis of amines by reacting diethylzinc with N-sulfonyl imines and N-diphenylphosphinoyl imines. Chiral amines were isolated with moderate to acceptable yields and enantioselectivities.
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Abstract The enantioselective reaction mentioned in the title is achieved in the presence of chiral amino alcohols.
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A series of sulfoxides were sulfoximinated using oxidative addition of 3-aminoquinazolinones by lead tetraacetate in the presence of hexamethyldisilazane. They were applied for the first time in catalytic enantioselective addition to aromatic aldehydes with a product enantiopurity (ee) of 92% in the case of 2-methoxybenzaldehyde.
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Abstract The enantioselective synthesis of P ‐stereogenic chiral organophosphines under organocatalysis is a challenging research field, and reports that use this approach are rare. Herein, we have developed the enantioselective synthesis of P ‐stereogenic chiral oxazaphospholidines by using a bicyclic thiazole as the organocatalyst in the P–N and P–O bond‐forming reaction. The P ‐chiral products were prepared in high yields with moderate enantioselectivities. The base that was used in this process had a significant influence on the enantioselectivity of the reaction and in some cases led to the opposite configuration of the P ‐chiral center.
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Asymmetric catalysis is one of the most attractive and efficient approaches toward synthesis of chiral enantioenriched compounds using achiral compounds as substrates and reagents. Compared with the well-established enantioselective preparation of carbon-stereogenic compounds, the corresponding preparation of silicon-stereogenic compounds is much less explored. In fact, most of the available methods rely on the use of stoichiometric amounts of chiral reagents, and much less progress has been made on catalytic enantioselective synthesis from achiral compounds. This review article mainly focuses on our recent achievements in this research area through the use of a synthetic strategy that employs transition-metal-catalyzed enantioselective desymmetrization reactions of prochiral tetraorganosilanes.
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Abstract The enantioselective construction of all‐carbon quaternary stereocenters is one of the most challenging fields in asymmetric synthesis. An asymmetric desymmetrization strategy offers an indirect and efficient method for the formation of all‐carbon stereocenters. An enantioselective formation of cyano‐bearing all‐carbon quaternary stereocenters in 1,2,3,4,‐tetrahydroquinolines and 2,3,4,5‐tetrahydro‐1H‐benzo[ b ]azepines by copper‐catalyzed desymmetric N‐arylation is demonstrated. The cyano group at the prochiral center plays a key role for the high enantioselectivity and works as an important functional group for further transformations. DFT studies provide a model which successfully accounts for the origin of enantioselectivity.
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