用具有C-N键轴向手性的P -烯烃型手性配体催化与isatin的不对称烯丙基胺化反应。

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC

Beilstein Journal of Organic Chemistry Pub Date : 2025-05-23 eCollection Date: 2025-01-01 DOI:10.3762/bjoc.21.83

Natsume Akimoto, Kaho Takaya, Yoshio Kasashima, Kohei Watanabe, Yasushi Yoshida, Takashi Mino

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引用次数: 0

摘要

在这项研究中，我们在pd催化的烯丙基酯的不对称烯丙基胺化反应中实现了P，烯烃型手性配体(aR)-(-)-6，该配体在氮原子上含有一个环己基和一个肉桂基，以isatin衍生物11为亲核试剂。反应进行得很有效，生成了对映体选择性高到高的产物(S)-13。在1 mmol的规模下也成功进行了放大反应。此外，在FeCl3作为催化剂的情况下，将丙二腈加入到所得产物(S)-13a中，得到相应的丙二腈衍生物(S)-16，光学纯度没有任何损失。

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Pd-Catalyzed asymmetric allylic amination with isatin using a P,olefin-type chiral ligand with C-N bond axial chirality.

In this study, we implemented the P,olefin-type chiral ligand (aR)-(-)-6, which contains a cyclohexyl group and a cinnamoyl group on the nitrogen atom, in the Pd-catalyzed asymmetric allylic amination of allylic esters with isatin derivatives 11 as nucleophiles. The reaction proceeds efficiently, yielding the products (S)-13 with good-to-high enantioselectivity. A scale-up reaction was also successfully conducted at a 1 mmol scale. Additionally, when malononitrile was added to the resulting product (S)-13a in the presence of FeCl₃ as the catalyst, the corresponding malononitrile derivative (S)-16 was obtained without any loss in optical purity.

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来源期刊

Beilstein Journal of Organic Chemistry 化学-有机化学

CiteScore

4.90

自引率

3.70%

发文量

167

审稿时长

1.4 months

期刊介绍： The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.