Rhodium(III)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α,β-unsaturated aldehydes

Wang, Yi-Fan; Yu, Hao-Yun; Xu, Hao; Wang, Ya-Jie; Yang, Xiaodi; Wang, Yu-Hui; Tian, Ping; Lin, Guo-Qiang

doi:10.1016/j.cclet.2024.109520

Chinese Chemical Letters

2024

DOI: 10.1016/j.cclet.2024.109520

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Rhodium(III)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α,β-unsaturated aldehydes

Yi-Fan Wang,

Hao-Yun Yu,

Hao Xu

et al.

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2024

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Cited by 2 publications

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“…As part of our ongoing program to explore the transformations of cyclohexadienone-containing 1,6-difunctional compounds, we wish to present an intramolecular [3 + 2] annulation of cyclohexadienone-tethered ynals for the construction of the tricyclo[6.2.1.0 4,11 ]undecane scaffold. The process begins with the formation of a Breslow intermediate, and its resonance structure manifests as an NHC-allenolate intermediate.…”

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confidence: 99%

N-Heterocyclic Carbene-Catalyzed Formal Intramolecular [3 + 2] Annulations of Cyclohexadienone-Tethered Ynals

Wang,

Kang,

Zhao

et al. 2024

Org. Lett.

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A formal [3 + 2] annulation of cyclohexadienone-tethered ynals is enabled by an N-heterocyclic carbene (NHC) catalyst, affording a tricyclo[6.2.1.0 4,11 ]undecane framework. This study represents the first demonstration of using C�C double bonds as the reaction partner in the NHC-catalyzed annulation of ynals. This strategy is characterized by mild reaction conditions and 100% atom economy as well as high catalytic performance and efficiency.

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confidence: 99%

N-Heterocyclic Carbene-Catalyzed Formal Intramolecular [3 + 2] Annulations of Cyclohexadienone-Tethered Ynals

Wang,

Kang,

Zhao

et al. 2024

Org. Lett.

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Advances in Chiral Pincer Complexes: Insights and Applications in Catalytic Asymmetric Reactions

Musa,

Peretz,

Dinnar

2024

IJMS

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Chiral pincer complexes, characterized by their rigid tridentate coordination framework, have emerged as powerful catalysts in asymmetric synthesis. This review provides a comprehensive overview of recent advancements in the development of chiral pincer-type ligands and their corresponding transition metal complexes. We highlight the latest progress in their application across a range of catalytic asymmetric reactions, including the (transfer) hydrogenation of polar and non-polar bonds, hydrophosphination, alkynylation, Friedel-Crafts reactions, enantioselective reductive cyclization of alkynyl-tethered cyclohexadienones, enantioselective hydrosilylation, as well as Aza–Morita–Baylis–Hillman reactions. The structural rigidity and tunability of chiral pincer complexes enable precise control over stereoselectivity, resulting in high enantioselectivity and efficiency in complex molecular transformations. As the field advances, innovations in ligand design and the exploration of new metal centers are expected to expand the scope and utility of these catalysts, bearing significant implications for the synthesis of enantioenriched compounds in pharmaceuticals, materials science, and beyond.

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Rhodium(III)-catalyzed diastereo- and enantioselective hydrosilylation/cyclization reaction of cyclohexadienone-tethered α,β-unsaturated aldehydes

Cited by 2 publications

References 40 publications

N-Heterocyclic Carbene-Catalyzed Formal Intramolecular [3 + 2] Annulations of Cyclohexadienone-Tethered Ynals

N-Heterocyclic Carbene-Catalyzed Formal Intramolecular [3 + 2] Annulations of Cyclohexadienone-Tethered Ynals

Advances in Chiral Pincer Complexes: Insights and Applications in Catalytic Asymmetric Reactions

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