实现氮内酯与烯酸酯的不对称 β 选择性加成反应

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC Beilstein Journal of Organic Chemistry Pub Date : 2024-07-04 DOI:10.3762/bjoc.20.134

Behzad Nasiri, Ghaffar Pasdar, Paul Zebrowski, Katharina Röser, David Naderer, Mario Waser

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引用次数: 0

摘要

摘要我们在此报告氮内酯与烯酸盐的不对称有机催化加成。在使用手性季铵盐催化剂（即 Maruoka’的二萘基螺环铵盐）时，各种氮内酯以中等水平的对映选择性（高达 83:17er）以β选择性的方式加成到烯酸盐。此外，得到的产物可以成功地参与亲核开环反应，从而得到高度官能化的 α-氨基酸衍生物。Chem.2024, 20, 1504–1509. doi:10.3762/bjoc.20.134

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Towards an asymmetric β-selective addition of azlactones to allenoates

Abstract

We herein report the asymmetric organocatalytic addition of azlactones to allenoates. Upon using chiral quaternary ammonium salt catalysts, i.e., Maruoka’s binaphthyl-based spirocyclic ammonium salts, the addition of various azlactones to allenoates proceeds in a β-selective manner with moderate levels of enantioselectivities (up to 83:17 er). Furthermore, the obtained products can be successfully engaged in nucleophilic ring opening reactions, thus giving highly functionalized α-amino acid derivatives.

Beilstein J. Org. Chem. 2024, 20, 1504–1509. doi:10.3762/bjoc.20.134

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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.