Organocatalytic Enantioselective Arylation to Access\nDensely Aryl-Substituted P‑Stereogenic Centers

Although\nmethods for synthesizing chiral phosphorus scaffolds are\navailable, the potential of this molecular chirality remains largely\nunexplored. Herein, we present a remote desymmetrization of prochiral\nbiaryl phosphine oxides through an organocatalytic asymmetric arylation.\nThis metal-free approach enables the efficient synthesis of a wide\nrange of densely functionalized P(V)-stereogenic compounds with good\nto excellent yields and satisfactory enantioselectivities. Mechanistic\nstudies reveal that hydrogen bonding and ion-pairing interactions\nare crucial for achieving precise stereocontrol in this transformation.

Publication Details

Journal
Figshare
Published
2024-12-23
DOI
https://doi.org/10.1021/acs.orglett.4c03992.s001
Primary Topic
Asymmetric Hydrogenation and Catalysis
Type
article
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article

Organocatalytic Enantioselective Arylation to Access\nDensely Aryl-Substituted P‑Stereogenic Centers

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Asymmetric Hydrogenation and Catalysis
article

Organocatalytic Enantioselective Arylation to Access\nDensely Aryl-Substituted P‑Stereogenic Centers

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Abstract

Although\nmethods for synthesizing chiral phosphorus scaffolds are\navailable, the potential of this molecular chirality remains largely\nunexplored. Herein, we present a remote desymmetrization of prochiral\nbiaryl phosphine oxides through an organocatalytic asymmetric arylation.\nThis metal-free approach enables the efficient synthesis of a wide\nrange of densely functionalized P(V)-stereogenic compounds with good\nto excellent yields and satisfactory enantioselectivities. Mechanistic\nstudies reveal that hydrogen bonding and ion-pairing interactions\nare crucial for achieving precise stereocontrol in this transformation.

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Asymmetric Hydrogenation and Catalysis
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Organocatalytic Enantioselective Arylation to Access\nDensely Aryl-Substituted P‑Stereogenic Centers · Figshare (2024) | TGRS Research Map | TGRS