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

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-12-30 DOI:10.1021/acs.orglett.4c04007
Qingyu Tian, Jin Ge, Yaopeng Liu, Xi Wu, Zhenghao Li, Guolin Cheng
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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.

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钯催化前手性磷酰胺和芳基碘化物非对称环化对映选择性合成P(V)-立体化合物
P(V)-立体化合物的对映选择性合成已成为一个有趣的研究课题,主要是因为它们具有显著的生物活性和广阔的应用前景。在此,我们公开了一种通过钯和手性降冰片烯催化的不对称环法制取前手性磷酰胺和芳基碘化物的P(V)-立体化合物的方法。P(V)-立体化合物形成范围广,对映体过量性好。值得注意的是,利用产物上的C-Br键作为多用途的关键亲电试剂,通过多种过渡金属催化的交叉偶联反应证明了该方法的合成价值。
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来源期刊
Organic Letters
Organic Letters 化学-有机化学
CiteScore
9.30
自引率
11.50%
发文量
1607
审稿时长
1.5 months
期刊介绍: Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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