源自 SPINOL 的手性磷酸硼催化外环 α、β-不饱和酮的 1,4-不对称还原反应

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-10-14 DOI:10.1002/adsc.202401008

Wenhui Cui, Fanjing Meng, Zengfeng Zhang, Zhuting Han, Yang Cao

{"title":"源自 SPINOL 的手性磷酸硼催化外环 α、β-不饱和酮的 1,4-不对称还原反应","authors":"Wenhui Cui, Fanjing Meng, Zengfeng Zhang, Zhuting Han, Yang Cao","doi":"10.1002/adsc.202401008","DOIUrl":null,"url":null,"abstract":"An asymmetric 1,4-reduction of exocyclic α,β-unsaturated ketones leading to the formation of diverse optically active α-substituted tetralones has been realized by chiral SPINOL-derived boro-phosphate. The enantios-elctivity-determining step of the reaction is the protonation of a highly active boron enolates intermediate. The catalytic reduction system composed of chiral SPINOL-derived boro-phosphate and pinacolborane may be widely used in other asymmetric reduction reactions.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"84 1","pages":""},"PeriodicalIF":4.4000,"publicationDate":"2024-10-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Chiral SPINOL-derived Boro-phosphate-Catalyzed Asymmetric 1,4-Reduction of Exocyclic α,β-Unsaturated Ketones\",\"authors\":\"Wenhui Cui, Fanjing Meng, Zengfeng Zhang, Zhuting Han, Yang Cao\",\"doi\":\"10.1002/adsc.202401008\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"An asymmetric 1,4-reduction of exocyclic α,β-unsaturated ketones leading to the formation of diverse optically active α-substituted tetralones has been realized by chiral SPINOL-derived boro-phosphate. The enantios-elctivity-determining step of the reaction is the protonation of a highly active boron enolates intermediate. The catalytic reduction system composed of chiral SPINOL-derived boro-phosphate and pinacolborane may be widely used in other asymmetric reduction reactions.\",\"PeriodicalId\":118,\"journal\":{\"name\":\"Advanced Synthesis & Catalysis\",\"volume\":\"84 1\",\"pages\":\"\"},\"PeriodicalIF\":4.4000,\"publicationDate\":\"2024-10-14\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Advanced Synthesis & Catalysis\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1002/adsc.202401008\",\"RegionNum\":2,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, APPLIED\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/adsc.202401008","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}

引用次数: 0

摘要

手性 SPINOL 衍生的硼磷酸盐实现了外环 α、β-不饱和酮的不对称 1,4-还原，从而形成了多种具有光学活性的 α-取代的四氢萘酮。该反应的对映活性决定性步骤是高活性硼烯酸盐中间体的质子化。由衍生自手性 SPINOL 的硼磷酸盐和频哪醇硼烷组成的催化还原体系可广泛用于其他不对称还原反应。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

Chiral SPINOL-derived Boro-phosphate-Catalyzed Asymmetric 1,4-Reduction of Exocyclic α,β-Unsaturated Ketones

An asymmetric 1,4-reduction of exocyclic α,β-unsaturated ketones leading to the formation of diverse optically active α-substituted tetralones has been realized by chiral SPINOL-derived boro-phosphate. The enantios-elctivity-determining step of the reaction is the protonation of a highly active boron enolates intermediate. The catalytic reduction system composed of chiral SPINOL-derived boro-phosphate and pinacolborane may be widely used in other asymmetric reduction reactions.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.