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 phosphina...

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Published inOrganic letters Vol. 27; no. 1; pp. 121 - 128
Main Authors Tian, Qingyu, Ge, Jin, Liu, Yaopeng, Wu, Xi, Li, Zhenghao, Cheng, Guolin
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 10.01.2025
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ASYMMETRIC-SYNTHESIS
OXIDES
BIOSYNTHESIS
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Summary: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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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c04007