Palladium-Catalyzed Enantioselective Synthesis of P(V)-Stereogenic Compounds via Desymmetric Annulation of Prochiral Phosphinamides and Aryl Iodides

The enantioselective synthesis of P(V)-stereogenic compounds has emerged as an interesting research topic primarily due to their significant biological activity and broad application prospects. Herein, we disclose a method for the construction of P(V)-stereogenic compounds from prochiral phosphinamides and aryl iodides via palladium- and chiral norbornene-catalyzed desymmetric annulation. The P(V)-stereogenic compounds were formed with a broad scope with excellent enantiomeric excesses. It is noteworthy that the synthetic value of this procedure was proven by a variety of transition metal-catalyzed cross-coupling reactions using the C-Br bond on the product as a versatile linchpin electrophile.

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Publication Details

Journal
Organic Letters
Published
2024-12-30
DOI
https://doi.org/10.1021/acs.orglett.4c04007
Citations
5
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
1.25

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article

Palladium-Catalyzed Enantioselective Synthesis of P(V)-Stereogenic Compounds via Desymmetric Annulation of Prochiral Phosphinamides and Aryl Iodides

Guolin Cheng, Jin Ge, Yaopeng Liu, Qingyu Tian et al.
5 citations
Organic Letters
Catalytic C–H Functionalization Methods
1.25
article

Palladium-Catalyzed Enantioselective Synthesis of P(V)-Stereogenic Compounds via Desymmetric Annulation of Prochiral Phosphinamides and Aryl Iodides

Guolin Cheng, Jin Ge, Yaopeng Liu, Qingyu Tian, Xi Wu, Zhenghao Li
article en
5 citations

Abstract

The enantioselective synthesis of P(V)-stereogenic compounds has emerged as an interesting research topic primarily due to their significant biological activity and broad application prospects. Herein, we disclose a method for the construction of P(V)-stereogenic compounds from prochiral phosphinamides and aryl iodides via palladium- and chiral norbornene-catalyzed desymmetric annulation. The P(V)-stereogenic compounds were formed with a broad scope with excellent enantiomeric excesses. It is noteworthy that the synthetic value of this procedure was proven by a variety of transition metal-catalyzed cross-coupling reactions using the C-Br bond on the product as a versatile linchpin electrophile.

Organic LettersVol. 27(1)
Huaqiao University (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 21%
Catalytic C–H Functionalization Methods
1.25
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