2018Journal of Synthetic Organic Chemistry JapanOpen access

Catalytic Asymmetric Synthesis of Silicon-Stereogenic Compounds by Enantioselective Desymmetrization of Prochiral Tetraorganosilanes

Ryo Shintani

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Abstract

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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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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Available abstract

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.

Key concepts: Enantioselective synthesis, Stereocenter, Desymmetrization, Catalysis, Reagent, Chemistry, Organic chemistry, Combinatorial chemistry

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