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
更新
PDF的下载单位、IP信息已删除 (2025-6-4)

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
科研通AI5应助WJH采纳,获得10
1秒前
Zard发布了新的文献求助10
1秒前
王冉冉完成签到,获得积分10
2秒前
ryan1300完成签到 ,获得积分10
2秒前
易拉罐完成签到,获得积分10
2秒前
ZQ完成签到,获得积分10
2秒前
yyds完成签到,获得积分20
2秒前
2秒前
3秒前
彭于晏应助刘宇采纳,获得10
3秒前
4秒前
leeom发布了新的文献求助10
6秒前
Timo干物类完成签到,获得积分10
6秒前
北冥有鱼给北冥有鱼的求助进行了留言
6秒前
6秒前
王冉冉发布了新的文献求助30
6秒前
Ava应助易拉罐采纳,获得10
7秒前
隐形曼青应助无心的土豆采纳,获得10
7秒前
乐于助人大好人完成签到 ,获得积分10
7秒前
ZZQ完成签到,获得积分10
11秒前
量子星尘发布了新的文献求助10
11秒前
Lina HE完成签到 ,获得积分10
11秒前
852应助科研通管家采纳,获得10
11秒前
Ava应助科研通管家采纳,获得10
12秒前
ED应助科研通管家采纳,获得10
12秒前
领导范儿应助科研通管家采纳,获得10
12秒前
12秒前
Akim应助科研通管家采纳,获得10
12秒前
进步完成签到,获得积分10
12秒前
852应助科研通管家采纳,获得10
12秒前
ED应助科研通管家采纳,获得10
12秒前
英俊的铭应助科研通管家采纳,获得10
12秒前
SciGPT应助科研通管家采纳,获得10
12秒前
Akim应助科研通管家采纳,获得10
12秒前
iNk应助dh采纳,获得20
12秒前
orixero应助科研通管家采纳,获得30
12秒前
思源应助科研通管家采纳,获得10
12秒前
wanci应助科研通管家采纳,获得10
12秒前
赘婿应助科研通管家采纳,获得10
13秒前
wanci应助科研通管家采纳,获得10
13秒前
高分求助中
【提示信息,请勿应助】关于scihub 10000
Les Mantodea de Guyane: Insecta, Polyneoptera [The Mantids of French Guiana] 3000
徐淮辽南地区新元古代叠层石及生物地层 3000
The Mother of All Tableaux: Order, Equivalence, and Geometry in the Large-scale Structure of Optimality Theory 3000
Global Eyelash Assessment scale (GEA) 1000
Picture Books with Same-sex Parented Families: Unintentional Censorship 550
Research on Disturbance Rejection Control Algorithm for Aerial Operation Robots 500
热门求助领域 (近24小时)
化学 材料科学 医学 生物 工程类 有机化学 生物化学 物理 内科学 纳米技术 计算机科学 化学工程 复合材料 遗传学 基因 物理化学 催化作用 冶金 细胞生物学 免疫学
热门帖子
关注 科研通微信公众号,转发送积分 4038569
求助须知:如何正确求助?哪些是违规求助? 3576279
关于积分的说明 11374944
捐赠科研通 3305979
什么是DOI,文献DOI怎么找? 1819354
邀请新用户注册赠送积分活动 892698
科研通“疑难数据库(出版商)”最低求助积分说明 815048