Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, School of Science, Westlake University, 18 Shilongshan Road, Hangzhou 310024, Zhejiang Province, China.
Institute of Natural Sciences, Westlake Institute for Advanced Study, 18 Shilongshan Road, Hangzhou 310024, Zhejiang Province, China.
J Am Chem Soc. 2021 Mar 24;143(11):4154-4161. doi: 10.1021/jacs.1c00622. Epub 2021 Mar 10.
Chiral -branched amines are common structural motifs in functional materials, pharmaceuticals, and chiral catalysts. Therefore, developing efficient methods for preparing compounds with these privileged scaffolds is an important endeavor in synthetic chemistry. Herein, we describe an atom-economical, modular method for a nickel-catalyzed enantioselective α-alkenylation of readily available linear -sulfonyl amines with alkynes to afford a wide variety of allylic amines without the need for exogenous oxidants, reductants, or activating reagents. The method provides a platform for constructing chiral α-branched amines as well as derivatives such as α-amino amides and β-amino alcohols, which can be conveniently accessed from the newly introduced alkene. Given the generality, versatility, and high atom economy of this method, we anticipate that it will have broad synthetic utility.
手性支化胺是功能材料、药物和手性催化剂中的常见结构基序。因此，开发有效方法来制备具有这些优势骨架的化合物是合成化学中的重要任务。在此，我们描述了一种原子经济性的、模块化的镍催化方法，用于对易得的线性 -磺酰基胺与炔烃进行对映选择性的α-烯丙基化反应，以提供广泛的各种烯丙基胺，而无需使用外源氧化剂、还原剂或活化试剂。该方法为构建手性α-支化胺以及α-氨基酰胺和β-氨基醇等衍生物提供了一个平台，这些衍生物可以方便地从新引入的烯烃中获得。鉴于该方法的通用性、多功能性和高原子经济性，我们预计它将具有广泛的合成用途。
