镍催化的 1,3-二烯与醛的不对称 Borylative 耦合

IF 1.7 4区化学 Q3 CHEMISTRY, ORGANIC

Synlett Pub Date : 2024-03-13 DOI:10.1055/a-2275-3719

{"title":"镍催化的 1,3-二烯与醛的不对称 Borylative 耦合","authors":"","doi":"10.1055/a-2275-3719","DOIUrl":null,"url":null,"abstract":"The nickel-catalyzed borylative coupling of aldehydes and 1,3-dienes with diboron reagents offers an efficient method for synthesizing valuable homoallylic alcohols from easily accessible starting materials. However, achieving enantioselectivity in this reaction has been a significant challenge. We discuss our recent report on the first example of a nickel-catalyzed enantioselective borylative coupling of aldehydes with 1,3-dienes, employing a chiral spiro-phosphine–oxazoline ligand. Notably, by utilizing (E)-1,3-dienes or (Z)-1,3-dienes, we can reverse the diastereoselectivity, yielding either anti- or syn-products, respectively.","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"16 1","pages":""},"PeriodicalIF":1.7000,"publicationDate":"2024-03-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Nickel-Catalyzed Asymmetric Borylative Coupling of 1,3-Dienes with Aldehydes\",\"authors\":\"\",\"doi\":\"10.1055/a-2275-3719\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"The nickel-catalyzed borylative coupling of aldehydes and 1,3-dienes with diboron reagents offers an efficient method for synthesizing valuable homoallylic alcohols from easily accessible starting materials. However, achieving enantioselectivity in this reaction has been a significant challenge. We discuss our recent report on the first example of a nickel-catalyzed enantioselective borylative coupling of aldehydes with 1,3-dienes, employing a chiral spiro-phosphine–oxazoline ligand. Notably, by utilizing (E)-1,3-dienes or (Z)-1,3-dienes, we can reverse the diastereoselectivity, yielding either anti- or syn-products, respectively.\",\"PeriodicalId\":22319,\"journal\":{\"name\":\"Synlett\",\"volume\":\"16 1\",\"pages\":\"\"},\"PeriodicalIF\":1.7000,\"publicationDate\":\"2024-03-13\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Synlett\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1055/a-2275-3719\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synlett","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1055/a-2275-3719","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

镍催化的醛和 1,3-二烯与二硼试剂的硼酸化偶联反应为从容易获得的起始材料中合成有价值的均烯醇提供了一种有效的方法。然而，在这一反应中实现对映选择性一直是一个重大挑战。我们讨论了最近关于镍催化的醛与 1,3-二烯的对映选择性硼烷化偶联反应的第一个实例，该反应采用了手性螺膦噁唑啉配体。值得注意的是，通过使用(E)-1,3-二烯或(Z)-1,3-二烯，我们可以逆转非对映选择性，分别得到反产物或合成产物。

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

Nickel-Catalyzed Asymmetric Borylative Coupling of 1,3-Dienes with Aldehydes

The nickel-catalyzed borylative coupling of aldehydes and 1,3-dienes with diboron reagents offers an efficient method for synthesizing valuable homoallylic alcohols from easily accessible starting materials. However, achieving enantioselectivity in this reaction has been a significant challenge. We discuss our recent report on the first example of a nickel-catalyzed enantioselective borylative coupling of aldehydes with 1,3-dienes, employing a chiral spiro-phosphine–oxazoline ligand. Notably, by utilizing (E)-1,3-dienes or (Z)-1,3-dienes, we can reverse the diastereoselectivity, yielding either anti- or syn-products, respectively.

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

Synlett 化学-有机化学

CiteScore

3.40

自引率

5.00%

发文量

369

审稿时长

1 months

期刊介绍： SYNLETT is an international journal reporting research results and current trends in chemical synthesis in short personalized reviews and preliminary communications. It covers all fields of scientific endeavor that involve organic synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines and offers the possibility to publish scientific primary data.