Chiral spirosiladiphosphines: ligand development and applications in Rh-catalyzed asymmetric hydrosilylation/cyclization of 1,6-enynes with enhanced reactivity

Hou, Fei; Liu, Minjie; Ru, Tong; Tan, Zequn; Ning, Yingtang; Chen, Fen‐Er

doi:10.1039/d2sc06349b

Cited by 7 publications

(3 citation statements)

References 62 publications

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“…Similar results were also obtained by Chen, Ning and co-workers in their synthesis of 26 using SPSiP 18. [18]…”

Section: Hydrosilylation Of Alkenementioning

confidence: 99%

Recent Progress in the Synthesis of Silaspiranes

Chen,

Hu,

Wang

et al. 2023

Chemistry A European J

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Silaspiranes bearing a spiro‐silicon center are promising ring frameworks for the synthesis of novel spirocyclic molecules possessing unique properties. Development of efficient methods towards these ring structures has therefore attracted considerable attentions of synthetic chemists. This minireview highlights the representative advances in the field, and is categorized into four parts according to the ring formation strategies: cyclization, annulation, ring expansion and cycloaddition.

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“…Similar results were also obtained by Chen, Ning and co-workers in their synthesis of 26 using SPSiP 18. [18]…”

Section: Hydrosilylation Of Alkenementioning

confidence: 99%

Recent Progress in the Synthesis of Silaspiranes

Chen,

Hu,

Wang

et al. 2023

Chemistry A European J

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“…To this end, we have previously investigated the hydrosilylation/cyclization reaction of 1,6-enynes using various ligand scaffolds. 17 We and Wang 18 demonstrated that novel Sicentered spirodiphosphine L1 featuring a large bite angle substantially enhanced the catalytic activity while maintaining a high level of enantioselectivity. Thus, we sought to explore the effect of the unique coordination structure of L1 in the hydroboration/cyclization sequence.…”

mentioning

confidence: 99%

“…In particular, appropriate chiral ligands are crucial for the successful cycloisomerization and related reductive cyclization of 1,6-enynes. To this end, we have previously investigated the hydrosilylation/cyclization reaction of 1,6-enynes using various ligand scaffolds . We and Wang demonstrated that novel Si-centered spirodiphosphine L1 featuring a large bite angle substantially enhanced the catalytic activity while maintaining a high level of enantioselectivity.…”

mentioning

confidence: 99%

Rhodium-Catalyzed Asymmetric Hydroboration/Cyclization of 1,6-Enynes Enabled by Spirosiladiphosphine Ligands: Constructing Chiral Five-Membered Rings with a Boron Handle

Hou,

Ning,

Song

et al. 2023

Org. Lett.

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A rhodium-catalyzed enantioselective hydroboration/cyclization reaction of 1,6-enynes is achieved by employing a spirosiladiphosphine ligand. The process allows the synthesis of five-membered hetero-and carbocycles bearing a boron handle with high levels of activity and selectivity. Various enynes and organoboranes (HBdan, HBpin, HBmp, and HBamm) have been accommodated, and enynes containing terminal alkynes have been integrated into the process for the first time. The high yields and selectivities of the transformation highlight the synthetic utility of these novel spirosiladiphosphine ligands. R hodium-catalyzed asymmetric cyclization of 1,6-enynes has emerged as a powerful and atom-economical approach to generate chiral hetero-and carbocycles. 1 This process often integrates additional transformations, such as hydrogenation and hydrofunctionalization, to facilitate consecutive C−X and C−C bond-forming events (Scheme 1A). 2 In this line, Ojima 3 first reported the hydrosilative cyclization of 1,6-enynes. Subsequent contributions from Chung, 4 Widenhoefer, 5 Zhou, 6 and others 7 have enabled the reaction to proceed with enhanced efficiency and superior enantiocontrol.

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

Wang,

Yu,

et al. 2024

Chinese Chemical Letters

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Chiral spirosiladiphosphines: ligand development and applications in Rh-catalyzed asymmetric hydrosilylation/cyclization of 1,6-enynes with enhanced reactivity

Abstract: Spirodiphosphines have been successfully applied in various asymmetric catalytic transformations. However, controlling the coordinating conformations by the direct displacement of the spiro atom remains elusive. Herein, we report the application...

Cited by 7 publications

References 62 publications

Recent Progress in the Synthesis of Silaspiranes

Recent Progress in the Synthesis of Silaspiranes

Rhodium-Catalyzed Asymmetric Hydroboration/Cyclization of 1,6-Enynes Enabled by Spirosiladiphosphine Ligands: Constructing Chiral Five-Membered Rings with a Boron Handle

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

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