Enantioselective α-Allylation of Aryl Acetic Acid Esters via C1-Ammonium Enolate Nucleophiles: Identification of a Broadly Effective Palladium Catalyst for Electron-Deficient Electrophiles,ACS Catalysis

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Enantioselective α-Allylation of Aryl Acetic Acid Esters via C1-Ammonium Enolate Nucleophiles: Identification of a Broadly Effective Palladium Catalyst for Electron-Deficient Electrophiles
ACS Catalysis ( IF 11.3 ) Pub Date : 2018-09-27 00:00:00 , DOI: 10.1021/acscatal.8b03507
Luke Hutchings-Goetz ₁ , Chao Yang ₁ , Thomas. N. Snaddon ₁

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We have identified a generally effective Pd catalyst for the highly enantioselective cooperative Lewis base/Pd-catalyzed α-allylation of aryl acetic esters using electron-deficient electrophiles. Changing between aldehyde, ketone, ester, and amide substituents at the terminus of intermediate cationic π-(allyl)Pd species affects both the efficiency of the reaction and, in the case of amides, control over the stereochemistry of the product alkene, as a function of the ligand. Tris[tri(2-thienyl)phosphino]Pd(0) serves as a broadly effective catalyst and overcomes these challenges to provide a general, high-yielding, and operationally simple C(sp³)–C(sp³) bond-forming method that gives products with high levels of enantioselectivity.

中文翻译：

通过C1-铵烯醇盐亲核试剂对芳族乙酸酯的对映选择性α-烯丙基化：对电子缺乏亲电试剂的广泛有效的钯催化剂的鉴定

我们已经确定了一种普遍有效的Pd催化剂，用于使用缺电子亲电试剂的高对映选择性路易斯碱/ Pd催化芳基乙酸酯的α-烯丙基化。在中间体阳离子π-（烯丙基）Pd物种末端处的醛，酮，酯和酰胺取代基之间的变化会影响反应效率，并且在酰胺的情况下，会控制产物烯烃的立体化学，例如配体的功能。Tris [tri（2-thienyl）phosphino] Pd（0）用作广泛有效的催化剂，克服了这些挑战，从而提供了一种通用，高产且操作简单的C（sp ³）–C（sp ³）键形成使产品具有高对映选择性的方法。

更新日期：2018-09-27

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