Cooperative activation of cyclobutanones and olefins leads to bridged ring systems by a catalytic [4 + 2] coupling

化学 分子内力 二烯 戒指(化学) 立体化学 催化作用 偶联反应 有机化学 天然橡胶
作者
Haye Min Ko,Guangbin Dong
出处
期刊:Nature Chemistry [Springer Nature]
卷期号:6 (8): 739-744 被引量:201
标识
DOI:10.1038/nchem.1989
摘要

Bridged ring systems are widely found in natural products, and successful syntheses of them frequently feature intramolecular Diels–Alder reactions. These reactions are subclassified as either type I or type II depending on how the diene motif is tethered to the rest of the substrate (type I are tethered at the 1-position of the diene and type II at the 2-position). Although the type I reaction has been used with great success, the molecular scaffolds accessible by the type II reactions are limited by the strain inherent in the formation of an sp2 carbon at a bridgehead position. Here, we describe a complementary approach that provides access to these structures through the C–C activation of cyclobutanones and their coupling with olefins. Various alkenes have been coupled with cyclobutanones to provide a range of bridged skeletons. The ketone group of the products serves as a convenient handle for downstream functionalization. Although widely used to form bridged ring systems, certain intramolecular Diels–Alder reactions are hampered by the strain inherent in forming an sp2-carbon at a bridgehead position. Now, an alternative strategy has been described to access these bridged ring systems through the C–C activation and coupling of cyclobutanones with olefins.
最长约 10秒,即可获得该文献文件

科研通智能强力驱动
Strongly Powered by AbleSci AI
科研通是完全免费的文献互助平台,具备全网最快的应助速度,最高的求助完成率。 对每一个文献求助,科研通都将尽心尽力,给求助人一个满意的交代。
实时播报
刚刚
卓哥发布了新的文献求助10
刚刚
科研通AI5应助sansan采纳,获得10
1秒前
1秒前
1秒前
脑洞疼应助杰森斯坦虎采纳,获得10
1秒前
3秒前
4秒前
研友_QQC完成签到,获得积分10
4秒前
NeuroWhite完成签到,获得积分10
4秒前
4秒前
搜索v完成签到,获得积分10
5秒前
liuchuck完成签到 ,获得积分10
5秒前
5秒前
5秒前
猫独秀完成签到,获得积分10
5秒前
7秒前
buno应助yuefeng采纳,获得10
7秒前
yiming完成签到,获得积分10
7秒前
落落发布了新的文献求助10
8秒前
清秋若月完成签到 ,获得积分10
8秒前
8秒前
呵呵呵呵完成签到,获得积分10
9秒前
9秒前
远方发布了新的文献求助10
10秒前
zxc111关注了科研通微信公众号
10秒前
11秒前
nanhe698发布了新的文献求助10
11秒前
Huang完成签到,获得积分10
11秒前
碳土不凡完成签到 ,获得积分10
12秒前
12秒前
淡淡采白发布了新的文献求助10
13秒前
13秒前
14秒前
Akim应助dingdong采纳,获得10
14秒前
14秒前
14秒前
satchzhao发布了新的文献求助10
14秒前
可爱的函函应助尺素寸心采纳,获得10
14秒前
66发布了新的文献求助10
15秒前
高分求助中
Continuum Thermodynamics and Material Modelling 3000
Production Logging: Theoretical and Interpretive Elements 2700
Social media impact on athlete mental health: #RealityCheck 1020
Ensartinib (Ensacove) for Non-Small Cell Lung Cancer 1000
Unseen Mendieta: The Unpublished Works of Ana Mendieta 1000
Bacterial collagenases and their clinical applications 800
El viaje de una vida: Memorias de María Lecea 800
热门求助领域 (近24小时)
化学 材料科学 生物 医学 工程类 有机化学 生物化学 物理 纳米技术 计算机科学 内科学 化学工程 复合材料 基因 遗传学 物理化学 催化作用 量子力学 光电子学 冶金
热门帖子
关注 科研通微信公众号,转发送积分 3527928
求助须知:如何正确求助?哪些是违规求助? 3108040
关于积分的说明 9287614
捐赠科研通 2805836
什么是DOI,文献DOI怎么找? 1540070
邀请新用户注册赠送积分活动 716904
科研通“疑难数据库(出版商)”最低求助积分说明 709808