ArticleNature communications2020
Stereospecific Si-C coupling and remote control of axial chirality by enantioselective palladium-catalyzed hydrosilylation of maleimides.
Article in Nature communications, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Enantiotopic-group-selective coupling for unified access to carbazole atropisomers as versatile chiral chromophores.Nature communications · 2025Article
- Copper-catalyzed intermolecular Regio- and Enantioselective Hydrosilylation of Alkenes with Prochiral Silanes.Nature communications · 2025Article
- The role of silicon in drug discovery: a review.RSC medicinal chemistry · 2024Review
- Access to distal biaxial atropisomers by iridium catalyzed asymmetric C-H alkylation.Chemical science · 2024Article
- Atroposelective catalysis.Nature reviews. Chemistry · 2024Review
- Atroposelective Synthesis of Aldehydes via Alcohol Dehydrogenase-Catalyzed Stereodivergent Desymmetrization.JACS Au · 2024Article
- Rhodium-catalyzed enantioselective and diastereodivergent access to diaxially chiral heterocycles.Nature communications · 2023Article
- Article
- Construction of Non-Biaryl Atropisomeric Amide Scaffolds Bearing a C-N Axis via Enantioselective Catalysis.Molecules (Basel, Switzerland) · 2022Review
- Simultaneous construction of axial and planar chirality by gold/TY-Phos-catalyzed asymmetric hydroarylation.Nature communications · 2021Article
Corrections and comments
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Authors and funding
9 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Hydrosilylation of unsaturated carbon-carbon bonds with hydrosilanes is a very important process to access organosilicon compounds and ranks as one of the most fundamental reactions in organic chemistry. However, catalytic asymmetric hydrosilylation of activated alkenes and internal alkenes has proven elusive, due to competing reduction of carbon-carbon double bond or isomerization processes. Herein, we report a highly enantioselective Si-C coupling by hydrosilylation of carbonyl-activated alkenes using a palladium catalyst with a chiral TADDOL-derived phosphoramidite ligand, which inhibits O-hydrosilylation/olefin reduction. The stereospecific Si-C coupling/hydrosilylation of maleimides affords a series of silyl succinimides with up to 99% yield, >99:1 diastereoselectivity and >99:1 enantioselectivity. The high degree of stereoselectivity exerts remote control of axial chirality, leading to functionalized, axially chiral succinimides which are versatile building blocks. The product utility is highlighted by the enantioselective construction of N-heterocycles bearing up to three stereocenters.
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Registered trials
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