硼烷催化的 2-烷基吡啶†的不对称还原

IF 5.5 1区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Chinese Journal of Chemistry Pub Date : 2024-08-08 DOI:10.1002/cjoc.202400671

Heng Luo, Zhao-Ying Yang, Ming Zhang, Xiao-Chen Wang

{"title":"硼烷催化的 2-烷基吡啶†的不对称还原","authors":"Heng Luo, Zhao-Ying Yang, Ming Zhang, Xiao-Chen Wang","doi":"10.1002/cjoc.202400671","DOIUrl":null,"url":null,"abstract":"<div>\n \n <p>Herein, a method for the enantioselective reduction of unprotected 2-alkylpyridines is reported for the first time. By using pinacolborane and an amide as reducing agents, a large number of 2-alkylpiperidines were synthesized with high yields and excellent enantioselectivities via a cascade process involving 1,4-hydroboration and subsequent transfer hydrogenation. The resulting products can be easily converted to natural alkaloids.</p>\n <p>\n </p>\n </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"42 23","pages":"3088-3092"},"PeriodicalIF":5.5000,"publicationDate":"2024-08-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Borane-Catalyzed Asymmetric Reduction of 2-Alkylpyridines†\",\"authors\":\"Heng Luo, Zhao-Ying Yang, Ming Zhang, Xiao-Chen Wang\",\"doi\":\"10.1002/cjoc.202400671\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div>\\n \\n <p>Herein, a method for the enantioselective reduction of unprotected 2-alkylpyridines is reported for the first time. By using pinacolborane and an amide as reducing agents, a large number of 2-alkylpiperidines were synthesized with high yields and excellent enantioselectivities via a cascade process involving 1,4-hydroboration and subsequent transfer hydrogenation. The resulting products can be easily converted to natural alkaloids.</p>\\n <p>\\n </p>\\n </div>\",\"PeriodicalId\":151,\"journal\":{\"name\":\"Chinese Journal of Chemistry\",\"volume\":\"42 23\",\"pages\":\"3088-3092\"},\"PeriodicalIF\":5.5000,\"publicationDate\":\"2024-08-08\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chinese Journal of Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://onlinelibrary.wiley.com/doi/10.1002/cjoc.202400671\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chinese Journal of Chemistry","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/cjoc.202400671","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}

引用次数: 0

摘要

本文首次报道了一种未受保护的 2-烷基吡啶的对映选择性还原方法。以频哪醇硼烷和酰胺为还原剂，通过 1,4-氢化和随后的转移氢化级联过程，合成了大量 2-烷基哌啶类化合物，产量高，对映选择性好。得到的产物可以很容易地转化为天然生物碱。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Borane-Catalyzed Asymmetric Reduction of 2-Alkylpyridines†

查看原文本刊更多论文

Borane-Catalyzed Asymmetric Reduction of 2-Alkylpyridines†

Herein, a method for the enantioselective reduction of unprotected 2-alkylpyridines is reported for the first time. By using pinacolborane and an amide as reducing agents, a large number of 2-alkylpiperidines were synthesized with high yields and excellent enantioselectivities via a cascade process involving 1,4-hydroboration and subsequent transfer hydrogenation. The resulting products can be easily converted to natural alkaloids.

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

Chinese Journal of Chemistry 化学-化学综合

CiteScore

8.80

自引率

14.80%

发文量

422

审稿时长

1.7 months

期刊介绍： The Chinese Journal of Chemistry is an international forum for peer-reviewed original research results in all fields of chemistry. Founded in 1983 under the name Acta Chimica Sinica English Edition and renamed in 1990 as Chinese Journal of Chemistry, the journal publishes a stimulating mixture of Accounts, Full Papers, Notes and Communications in English.