SIOC OpenIR  > 金属有机化学国家重点实验室
手性磷酸催化的C3取代吲哚和甲基乙烯基酮的不对称串联反应
Alternative TitleChiral Phosphoric Acid-Catalyzed Asymmetric Cascade Reaction Of C(3) Substituted Indoles and Methyl Vinyl Ketone
段德河1; 殷勤1; 王守国1; 顾庆1; 游书力1
2014
Source Publication化学学报
Volume72Issue:9Pages:1001-1004
Other AbstractFused indolines bearing a chiral quaternary carbon center at the C(3) position represent very important moieties widely existed in natural products and biologically active compounds. Various approaches to access these important scaffolds have been developed. Among them, asymmetric dearomatization\cyclization cascade reaction is the most concise and effective method by using indole derivatives as starting material. However, the documented reports mainly employed tryptamine or tryptophol derivatives, providing indoline products, such as pyrroloindolines or furoindolines. Therefore, the development of other type of indole derivatives allowing structural diversity is highly desirable. In this paper, an efficient asymmetric Michael addition\cyclization cascade reaction of indole derivatives with methyl vinyl ketone (MVK) was developed. After screening various phosphoric acids in the reaction of indole derivative (la) with MVK, this cascade reaction delivered the dearomative product (2a) in 77% yield and 95% enantiomeric excess in the presence of (R)-SPINOL-derived chiral phosphoric acid (R)-4c with 5 A molecular sieves as additive in CHCl3 at room temperature. Under the optimized reaction conditions, a wide range of substituted indole derivatives bearing both electron-donating and electron-withdrawing groups have been tested. In all cases, the cascade dearomatization reaction proceeded smoothly to afford their corresponding indolo[2,3-b]quinoline products in moderate to good yields and excellent enantioselectivity. The absolute configuration of the products was then determined as (5aR,10bR) by an X-ray crystallographic analysis of a single crystal of enantiopure 2m. Moreover, this catalytic system was also feasible in a gram-scale reaction without erosion of enantiomeric excess. 1.25 g of product 2a can be prepared under the identical conditions in 91% yield and 93% ee.
Subject Area金属有机化学
DOI10.6023/A14060497
URL查看原文
Indexed BySCI
Language中文
Citation statistics
Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/39120
Collection金属有机化学国家重点实验室
Corresponding Author游书力
Affiliation1.中科院上海有机化学研究所
2.康龙化成(西安)新药技术有限公司
3.天津化学化工协同创新中心
Recommended Citation
GB/T 7714
段德河,殷勤,王守国,等. 手性磷酸催化的C3取代吲哚和甲基乙烯基酮的不对称串联反应[J]. 化学学报,2014,72(9):1001-1004.
APA 段德河,殷勤,王守国,顾庆,&游书力.(2014).手性磷酸催化的C3取代吲哚和甲基乙烯基酮的不对称串联反应.化学学报,72(9),1001-1004.
MLA 段德河,et al."手性磷酸催化的C3取代吲哚和甲基乙烯基酮的不对称串联反应".化学学报 72.9(2014):1001-1004.
Files in This Item:
File Name/Size DocType Version Access License
2014520.pdf(620KB)期刊论文作者接受稿开放获取CC BY-NC-SAApplication Full Text
Related Services
Recommend this item
Bookmark
Usage statistics
Export to Endnote
Google Scholar
Similar articles in Google Scholar
[段德河]'s Articles
[殷勤]'s Articles
[王守国]'s Articles
Baidu academic
Similar articles in Baidu academic
[段德河]'s Articles
[殷勤]'s Articles
[王守国]'s Articles
Bing Scholar
Similar articles in Bing Scholar
[段德河]'s Articles
[殷勤]'s Articles
[王守国]'s Articles
Terms of Use
No data!
Social Bookmark/Share
All comments (0)
No comment.
 

Items in the repository are protected by copyright, with all rights reserved, unless otherwise indicated.