Catalytic Regio- and Enantioselective Boracarboxylation of Arylalkenes with CO₂ and Diboron

Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(5), P. 2888 - 2894

Published: Jan. 26, 2024

Catalytic asymmetric carboxylation of readily available alkenes with CO2, an abundant and sustainable one-carbon building block, that gives access to value-added α-stereogenic carboxylic acids in atom- step-economic manner is highly attractive. However, it has remained a formidable challenge for the synthetic community. Here, first example Cu-catalyzed regio- enantioselective boracarboxylation reaction on various arylalkenes diboron under atmospheric pressure CO2 described, which afforded variety chiral β-boron-functionalized α-aryl up 87% yield 97% ee mild conditions. Importantly, α-substituted could also be subject this protocol excellent enantiopurities, thereby rendering efficient approach generation enantioenriched α-chiral all-carbon quaternary center. Moreover, high functional group tolerance, scalable synthesis, facile bioactive compounds, like (−)-scopolamine, (−)-anisodamine, (−)-tropicamide, further demonstrated utility strategy.

Language: Английский

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Copper-catalyzed enantioselective diyne cyclizationviaC(sp²)–O bond cleavage

Chemical Science, Journal Year: 2023, Volume and Issue: 14(13), P. 3493 - 3500

Published: Jan. 1, 2023

A copper-catalyzed asymmetric cascade cyclization via C(sp 2 )–O bond cleavage is disclosed, affording a range of chromeno[3,4- c ]pyrroles bearing triaryl oxa-quaternary carbon stereocenter in high yields and enantioselectivities.

Language: Английский

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Copper-catalyzed enantioselective desymmetrizing C(sp2)–H functionalization of azide-ynamides via α-imino copper carbenes

Science China Chemistry, Journal Year: 2024, Volume and Issue: 67(9), P. 2982 - 2988

Published: July 3, 2024

Language: Английский

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Copper Catalyzed [3+2] Annulation Reaction of Exocyclic Sulfonyl Enamides for the Synthesis of N,O‐Spiroketal and Spiroketal

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(44)

Published: June 1, 2024

A copper-catalyzed [3+2] annulation reaction of exocyclic enamines/enol ethers with 1,4-benzoquinone esters has been developed, providing facile access to N,O-spiroketals and spiroketals under mild conditions broad substrate scope (26 examples, 71-94 % yields). Gram scale synthesis chemical transformations demonstrated that this method is potentially useful in the natural products drugs containing a N,O- spiroketal moiety. The chiral N,O-spiroketal could be obtained 98 ee after recrystallization, when SaBOX ligand was employed.

Language: Английский

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Strategies and Methods for the Catalytic Asymmetric Synthesis of Benzofuran/Benzopyran Fused Acetals: A Review

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(24), P. 4320 - 4333

Published: Nov. 17, 2023

Benzofuran- and benzopyran-fused polycyclic acetals are found in a variety of biologically active natural products. The synthetic methods toward this class heterocycles have fascinated one the most intensive pursuits total synthesis. Nevertheless, stereoselective towards rapid construction such skeletons still remain challenging for organic chemists. Significant progress has been made research area recent years, however, literature on enantioselective approaches to construct these molecules not fully reviewed. Driven by their intriguing complex scaffolds with potential usefulness, we compose advances review covering all important works field. We hope will promote future area.

Language: Английский

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Copper-catalyzed atroposelective formal [4+1] annulation of 1,2-diketones with vinyl cations

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(100), P. 14831 - 14834

Published: Jan. 1, 2023

A copper-catalyzed atroposelective formal [4+1] annulation of 1,2-diketones with diynes has been developed, affording axially chiral arylpyrroles bearing 1,3-dioxole moieties high enantioselectivities under mild conditions.

Language: Английский

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Asymmetric Henry Reaction Using Cobalt Complexes with Bisoxazoline Ligands Bearing Two Fluorous Tags

Molecules, Journal Year: 2023, Volume and Issue: 28(22), P. 7632 - 7632

Published: Nov. 16, 2023

The effect of the presence fluorous tags in bisoxazoline ligands on stereoselectivity cobalt-catalyzed asymmetric Henry reaction was investigated. In contrast to obtained with conventional nonfluorous ligands, using bidentate featuring two adjacent positions aromatic ring yielded a reversed stereoselectivity. also when were replaced alkyl chains equivalent length, albeit considerably lesser degree, highlighting tags.

Language: Английский

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Partially carbonized chiral polymer with Cu-bis(oxazoline) as efficient heterogeneous catalyst for asymmetric Henry reaction

New Journal of Chemistry, Journal Year: 2024, Volume and Issue: 48(24), P. 10794 - 10797

Published: Jan. 1, 2024

Through partially carbonizing the condensation polymer CB, Cu–CB-180 catalyst achieved excellent enantioselectivity and recyclability in heterogeneous asymmetric Henry reaction.

Language: Английский

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Copper-catalyzed intermolecular formal [4 + 1] annulation of 1,5-diynes with benzocyclobutenones

Tetrahedron Chem, Journal Year: 2024, Volume and Issue: 12, P. 100090 - 100090

Published: Aug. 14, 2024

Language: Английский

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Nickel‐Catalyzed Enantioselective Carbonyl Addition of Aryl Chlorides and Bromides to Aldehydes

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(47)

Published: June 7, 2024

Abstract The Ni‐catalyzed enantioselective addition reaction of aryl halides to aldehydes was studied with cyanobis(oxazoline) as chiral ligands and Mn reductant. Aryl heteroaryl bromides reacted phenyl aldehyde at room temperature produce dibenzyl alcohols in 16–99 % yields 53–92 ees. Moreover, the coupling chloride a variety aryl, alkyl demonstrated presence cyanobis(oxazoline)/Ni(II) 60 °C generally high moderate enantioselectivities.

Language: Английский

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