Enantioselective Synthesis of β-Aminoboronic Acids via Borylalkylation of Enamides

Journal of the American Chemical Society, Год журнала: 2024, Номер 146(24), С. 16639 - 16647

Опубликована: Июнь 10, 2024

Aminoboronic acids represent a class of significant compounds that have attracted attention in the fields drug discovery and organic synthesis. Despite notable progress their synthesis, efficient construction chiral β-aminoboronic with alkyl side chains remains challenging endeavor. Here, we introduce an unprecedented nickel-catalyzed asymmetric borylalkylation enamides, employing simple diamine ligand, readily available B2pin2, halides as coupling partners. This reaction serves platform for assembling diverse range acid derivatives flexible chains, displaying exceptional regio-, stereo-, enantioselectivities. Moreover, this transformation exhibits broad substrate scope remarkable tolerance toward various functional groups. Theoretical calculations demonstrate benzyl group on ligand is key to high enantiocontrol transformation. Additionally, exemplify practical application strategy through concise synthesis complex bioactive molecules.

Язык: Английский

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Enantioselective Copper-Catalyzed Three-Component Cascade Boronation–Dearomatization Reaction: Synthesis of Chiral Boron-Containing 1,4-Dihydropyridines

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Янв. 10, 2025

A three-component cascade boronation–dearomatization reaction of alkenes, a diboron compound, and pyridinium salt is diclosed, affording chiral boron-containing 1,4-dihyropyridines in high yields (≤98%) diastereoselectivity (≤10:1 dr), along with excellent enantioselectivity (typically >99% ee). The catalytic system performs efficiently at low catalyst loadings (1 mol %) was tested >50 examples, including some biologically active molecules.

Язык: Английский

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Enantioselective Aminosilylation of Alkenes by Palladium/Ming‐Phos‐Catalyzed Tandem Narasaka–Heck/Silylation Reaction

Advanced Science, Год журнала: 2024, Номер unknown

Опубликована: Июль 5, 2024

A Pd-catalyzed enantioselective aminosilylation of alkenes via tandem Aza-Heck/silylation reaction under Pd/Sadphos catalysis is disclosed. wide array oxime esters and silicon reagents are tolerated, furnishing the chiral pyrrolines bearing one quaternary or two contiguous stereocenters in good yield with high enantioselectivity. Not only terminal but also tri-substituented internal successfully participate reaction, delivering vicinal complete diastereoselectivity DFT study conducted to probe pathway origin enantioselectivity, which revealed that stereoinduction arises from weak interaction between aromatic ring substrate fragment naphthyl group ligand.

Язык: Английский

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Enantioselective Borylative Functionalization of Internal Alkenes: A Platform for Constructing Vicinal Stereocenters^†

Chinese Journal of Chemistry, Год журнала: 2024, Номер 42(24), С. 3588 - 3604

Опубликована: Ноя. 1, 2024

Comprehensive Summary Vicinal stereogenic centers are ubiquitous structural scaffolds in both natural products and synthetic compounds, yet their enantioselective construction remains a significant challenge organic synthesis. Organoboron compounds of paramount importance chemistry due to ability undergo facile transformations, yielding diverse essential chemical bonds such as carbon‐carbon, carbon‐oxygen, carbon‐nitrogen, carbon‐halogen bonds. Transition‐metal‐catalyzed asymmetric borylative functionalizations internal alkenes offer promising strategy for the installation two adjacent chiral across carbon‐carbon By leveraging versatile transformations newly introduced boryl unit, this approach holds great potential expanding diversity vicinal scaffolds. In concise review, we aim highlight recent advancements transition‐metal‐catalyzed alkenes, underscore utility constructing centers, discuss unsolved challenges future directions field. Key Scientists

Язык: Английский

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Copper-Catalyzed Asymmetric 1,2-Arylboration of Enamines: Ac-cess to Chiral Borate-Containing 3,3’-Disubstituted Isoindolinones

Organic & Biomolecular Chemistry, Год журнала: 2024, Номер 22(30), С. 6085 - 6089

Опубликована: Янв. 1, 2024

An enantioselective Cu-catalyzed 1,2-arylboration reaction of N -( o -iodobenzoyl)enamines with bis(pinacolato)diboron (B 2 pin ) is developed to access chiral borate-containing 3,3′-disubstituted isoindolinones.

Язык: Английский

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Cobalt-Catalyzed Enantioselective Reductive Addition of Ketimine with Cyclopropyl Chloride to Construct the Chiral Amino Esters Bearing Cyclopropyl Fragments

Organic Chemistry Frontiers, Год журнала: 2024, Номер 11(22), С. 6311 - 6318

Опубликована: Янв. 1, 2024

Co-catalyzed asymmetric reductive addition of ketimine with cyclopropyl chloride has been realized to access diverse chiral amino esters bearing fragments broad functional group tolerance and excellent enantioselectivities.

Язык: Английский

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