Pd-catalyzed asymmetric carbonyl alkynylation: Synthesis of axial chiral ynones

Jin, Long; Han, Jian; Fang, Dongmei; Wang, Min; Liao, Jian

doi:10.1016/j.cclet.2023.109212

Cited by 3 publications

(3 citation statements)

References 68 publications

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“…reactions, such as Suzuki-Miyaura, Heck, and Negishi couplings, has provided chemists with powerful tools to construct complex molecules efficiently. [14][15][16][17][18][19][20][21] These Pd-catalysed reactions are celebrated for their broad substrate scope, and excellent regio-and stereoselectivity, setting a high standard in the arsenal of synthetic chemistry. [22][23][24] Ni, with its similar electronic and catalytic properties to Pd, has emerged as a particularly promising candidate in this context.…”

Section: Fa-you Linmentioning

confidence: 99%

“…13 The development of Pd-catalysed cross-coupling reactions, such as Suzuki–Miyaura, Heck, and Negishi couplings, has provided chemists with powerful tools to construct complex molecules efficiently. 14–21 These Pd-catalysed reactions are celebrated for their broad substrate scope, and excellent regio- and stereoselectivity, setting a high standard in the arsenal of synthetic chemistry. 22–24…”

Section: Introductionmentioning

confidence: 99%

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Mechanistic insights into facilitating reductive elimination from Ni(ii) species

Qiao,

Lin,

et al. 2024

Chem. Commun.

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Section: Fa-you Linmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Mechanistic insights into facilitating reductive elimination from Ni(ii) species

Qiao,

Lin,

et al. 2024

Chem. Commun.

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“…In contrast, asymmetric synthesis is considered the most environmentally friendly and efficient scale-up approach, despite the need for the development of suitable chiral catalysts. Fortunately, many chemists have made significant strides in developing numerous asymmetric synthesis methods to create a diverse range of atropisomers [151][152][153][154][155][156][157][158][159][160][161][162][163][164][165][166][167][168] and these methodologies are continually evolving. Furthermore, some atropisomers, not covered in this review, such as those C▬B bonded, 168 C▬O bonded, 169 C▬S bonded 170 atropisomers, also been successfully synthesized, albeit without their activities being tested.…”

Section: Medium-sized Ring and Macrocycle Bioactive Atropisomersmentioning

confidence: 99%

Bioactive atropisomers: Unraveling design strategies and synthetic routes for drug discovery

Liu,

Zhao,

Liu

et al. 2024

Medicinal Research Reviews

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Atropisomerism, an expression of axial chirality caused by limited bond rotation, is a prominent aspect within the field of medicinal chemistry. It has been shown that atropisomers of a wide range of compounds, including established FDA‐approved drugs and experimental molecules, display markedly different biological activities. The time‐dependent reversal of chirality in atropisomers poses complexity and obstacles in the process of drug discovery and development. Nonetheless, recent progress in understanding atropisomerism and enhanced characterization methods have greatly assisted medicinal chemists in the effective development of atropisomeric drug molecules. This article provides a comprehensive review of their special design thoughts, synthetic routes, and biological activities, serving as a reference for the synthesis and biological evaluation of bioactive atropisomers in the future.

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Palladium-catalyzed difluorocarbene transfer enables access to enantioenriched chiral spirooxindoles

Nie,

Wu,

Zhan

et al. 2024

Nat Commun

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We disclose herein an unprecedented Pd-catalyzed difluorocarbene transfer reaction, which assembles a series of structurally interesting chiral spiro ketones with generally over 90% ee. Commercially available BrCF2CO2K serves as the difluorocarbene precursor, which is harnessed as a user-friendly and safe carbonyl source in this transformation. Preliminary mechanistic studies exclude the formation of free CO in the reaction process, and importantly, we also find that BrCF2CO2K outcompete gaseous CO and several common CO surrogates in this asymmetric process. The reaction mechanism, including the in-situ progressive release of the difluorocarbene, the rapid migratory insertion of ArPd(II) = CF2 species, and subsequent defluorination hydrolysis by water to introduce the carbonyl group, accounts for the overall high efficiency and uniqueness. This work clearly showcases the advantage and potential of the difluorocarbene in synthesis and supplies a mechanistically distinct route for asymmetric carbonylative cyclization reactions.

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Pd-catalyzed asymmetric carbonyl alkynylation: Synthesis of axial chiral ynones

Cited by 3 publications

References 68 publications

Mechanistic insights into facilitating reductive elimination from Ni(ii) species

Mechanistic insights into facilitating reductive elimination from Ni(ii) species

Bioactive atropisomers: Unraveling design strategies and synthetic routes for drug discovery

Palladium-catalyzed difluorocarbene transfer enables access to enantioenriched chiral spirooxindoles

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