Enantioselective Self‐Assembly of a Homochiral Tetrahedral Cage Comprising Only Achiral Precursors

对映选择合成 亚胺 外消旋化 对映体 自组装 化学 手性(物理) 胺气处理 同手性 立体化学 结晶学 有机化学 催化作用 手征对称破缺 物理 量子力学 Nambu–Jona Lasinio模型 夸克
作者
Yi-Xin Chen,Ze Cao,Tinglong Feng,Xiaobo Zhang,Zhaoyong Li,Xue Dong,Shaoying Huang,Yingchun Liu,Xiao‐Yu Cao,Andrew C.‐H. Sue,Chuanhui Peng,Xufeng Lin,Linjun Wang,Hao Li
出处
期刊:Angewandte Chemie [Wiley]
卷期号:63 (15) 被引量:3
标识
DOI:10.1002/anie.202400467
摘要

Abstract How Nature synthesizes enantiomerically pure substances from achiral or racemic resources remains a mystery. In this study, we aimed to emulate this natural phenomenon by constructing chiral tetrahedral cages through self‐assembly, achieved by condensing two achiral compounds–a trisamine and a trisaldehyde. The occurrence of intercomponent CH⋅⋅⋅π interactions among the phenyl building blocks within the cage frameworks results in twisted conformations, imparting planar chirality to the tetrahedrons. In instances where the trisaldehyde precursor features electron‐withdrawing ester side chains, we observed that the intermolecular CH⋅⋅⋅π forces are strong enough to prevent racemization. To attain enantioselective self‐assembly, a chiral amine was introduced during the imine formation process. The addition of three equivalents of chiral amino mediator to one equivalent of the achiral trisaldehyde precursor formed a trisimino intermediate. This chiral compound was subsequently combined with the achiral trisamino precursor, leading to an imine exchange reaction that releasing the chiral amino mediator and formation of the tetrahedral cage with an enantiomeric excess ( ee ) of up to 75 %, exclusively composed of achiral building blocks. This experimental observation aligns with theoretical calculations based on the free energies of related cage structures. Moreover, since the chiral amine was not consumed during the imine exchange cycle, it enabled the enantioselective self‐assembly of the tetrahedral cage for multiple cycles when new batches of the achiral trisaldehyde and trisamino precursors were successively added.
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
哈哈哈哈完成签到,获得积分10
刚刚
沧海泪发布了新的文献求助10
1秒前
小胡先森应助凤凰山采纳,获得10
1秒前
一一完成签到,获得积分10
1秒前
惠惠发布了新的文献求助10
1秒前
shotgod完成签到,获得积分20
2秒前
科研通AI5应助蕾子采纳,获得10
2秒前
happy杨完成签到 ,获得积分10
2秒前
lichaoyes发布了新的文献求助10
2秒前
2秒前
Owen应助通~采纳,获得10
2秒前
封闭货车发布了新的文献求助10
3秒前
3秒前
www发布了新的文献求助10
4秒前
4秒前
4秒前
4秒前
5秒前
shotgod发布了新的文献求助10
5秒前
ling玲完成签到,获得积分10
5秒前
奔奔发布了新的文献求助10
5秒前
SweepingMonk应助虚心盼晴采纳,获得10
6秒前
7秒前
汉堡包应助XXF采纳,获得10
7秒前
wzh完成签到,获得积分10
7秒前
海底落日完成签到,获得积分20
7秒前
8秒前
科研通AI5应助123采纳,获得30
8秒前
烟花应助pi采纳,获得10
9秒前
汉堡包应助小木木壮采纳,获得10
9秒前
9秒前
yl发布了新的文献求助30
9秒前
菲菲呀发布了新的文献求助10
9秒前
9秒前
科研通AI5应助禾泽采纳,获得30
10秒前
坚强的樱发布了新的文献求助10
10秒前
英俊梦槐完成签到,获得积分10
10秒前
123发布了新的文献求助10
11秒前
11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 3527849
求助须知:如何正确求助?哪些是违规求助? 3107938
关于积分的说明 9287239
捐赠科研通 2805706
什么是DOI,文献DOI怎么找? 1540033
邀请新用户注册赠送积分活动 716893
科研通“疑难数据库(出版商)”最低求助积分说明 709794