直接不对称还原胺化

IF 14.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Journal of the American Chemical Society Pub Date : 2009-07-28 DOI:10.1021/ja905143m

Dietrich Steinhuebel*, Yongkui Sun*, Kazuhiko Matsumura*, Noboru Sayo, Takao Saito

{"title":"直接不对称还原胺化","authors":"Dietrich Steinhuebel*, Yongkui Sun*, Kazuhiko Matsumura*, Noboru Sayo, Takao Saito","doi":"10.1021/ja905143m","DOIUrl":null,"url":null,"abstract":"Asymmetric reductive amination of β-keto amides catalyzed by the chiral catalyst Ru(OAc)2((R)-dm-segphos) produces unprotected β-amino amides with high yields and high enantioselectivities (94.7?99.5% ee). This “one-pot” methodology is general in substrate scope and has been successfully employed to produce sitagliptin with 99.5% ee and 91% assay yield. The excellent reaction efficiency is attributed to the remarkable tolerance to high concentrations of ammonium ion, the high chemoselectivity, and the high enantioselectivity (99.5% ee) of the Ru catalyst system.","PeriodicalId":49,"journal":{"name":"Journal of the American Chemical Society","volume":"131 32","pages":"11316–11317"},"PeriodicalIF":14.4000,"publicationDate":"2009-07-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1021/ja905143m","citationCount":"144","resultStr":"{\"title\":\"Direct Asymmetric Reductive Amination\",\"authors\":\"Dietrich Steinhuebel*, Yongkui Sun*, Kazuhiko Matsumura*, Noboru Sayo, Takao Saito\",\"doi\":\"10.1021/ja905143m\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Asymmetric reductive amination of β-keto amides catalyzed by the chiral catalyst Ru(OAc)2((R)-dm-segphos) produces unprotected β-amino amides with high yields and high enantioselectivities (94.7?99.5% ee). This “one-pot” methodology is general in substrate scope and has been successfully employed to produce sitagliptin with 99.5% ee and 91% assay yield. The excellent reaction efficiency is attributed to the remarkable tolerance to high concentrations of ammonium ion, the high chemoselectivity, and the high enantioselectivity (99.5% ee) of the Ru catalyst system.\",\"PeriodicalId\":49,\"journal\":{\"name\":\"Journal of the American Chemical Society\",\"volume\":\"131 32\",\"pages\":\"11316–11317\"},\"PeriodicalIF\":14.4000,\"publicationDate\":\"2009-07-28\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://sci-hub-pdf.com/10.1021/ja905143m\",\"citationCount\":\"144\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of the American Chemical Society\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/ja905143m\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of the American Chemical Society","FirstCategoryId":"92","ListUrlMain":"https://pubs.acs.org/doi/10.1021/ja905143m","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}

引用次数: 144

摘要

手性催化剂Ru(OAc)2((R)-dm-segphos)催化β-酮酰胺的不对称还原胺化反应，得到了产率高、对映选择性高(94.7 ~ 99.5% ee)的无保护β-氨基酰胺。这种“一锅法”在底物范围内是通用的，并已成功地用于生产西格列汀，其纯度为99.5%，测定收率为91%。优异的反应效率归因于Ru催化剂体系对高浓度铵离子的耐受性、高化学选择性和高对映选择性(99.5% ee)。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Direct Asymmetric Reductive Amination

查看原文本刊更多论文

Direct Asymmetric Reductive Amination

Asymmetric reductive amination of β-keto amides catalyzed by the chiral catalyst Ru(OAc)₂((R)-dm-segphos) produces unprotected β-amino amides with high yields and high enantioselectivities (94.7?99.5% ee). This “one-pot” methodology is general in substrate scope and has been successfully employed to produce sitagliptin with 99.5% ee and 91% assay yield. The excellent reaction efficiency is attributed to the remarkable tolerance to high concentrations of ammonium ion, the high chemoselectivity, and the high enantioselectivity (99.5% ee) of the Ru catalyst system.

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

Journal of the American Chemical Society 化学-化学综合

CiteScore

24.40

自引率

6.00%

发文量

2398

审稿时长

1.6 months

期刊介绍： The flagship journal of the American Chemical Society, known as the Journal of the American Chemical Society (JACS), has been a prestigious publication since its establishment in 1879. It holds a preeminent position in the field of chemistry and related interdisciplinary sciences. JACS is committed to disseminating cutting-edge research papers, covering a wide range of topics, and encompasses approximately 19,000 pages of Articles, Communications, and Perspectives annually. With a weekly publication frequency, JACS plays a vital role in advancing the field of chemistry by providing essential research.