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硫桥连[5]螺旋烯的有机催化氢键供体/路易斯碱（HBD/LB）合成及手性光学性质

Organocatalytic hydrogen bond donor/Lewis base (HBD/LB) synthesis and chiroptical properties of thiabridged [5]helicenes.

作者信息

Lupi Michela, Fabbri Mosè, Mazzeo Giuseppe, Longhi Giovanna, Abbate Sergio, Viglianisi Caterina, Menichetti Stefano

机构信息

Department of Chemistry "Ugo Schiff" (DICUS), University of Florence, Via della Lastruccia 13, Sesto Fiorentino (FI), 50019 Florence, Italy.

Department of Molecular and Translational Medicine (DMMT), University of Brescia, V. le Europa 11, Brescia (BS), 25121 Brescia, Italy.

出版信息

Org Biomol Chem. 2024 Sep 11;22(35):7154-7163. doi: 10.1039/d4ob00979g.

DOI:10.1039/d4ob00979g
PMID:39040026
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11393524/
Abstract

Thiabridged [5]helicenes are obtained from thioaryl--phthalimido benzo[]phenothiazines using a hydrogen bond donor/Lewis base organocatalytic approach. Resolution of [5]helicenes using either (1)-(-)-camphanic acid as a chiral auxiliary or CSP-HPLC is reported. Thiabridged [5]helicenes show an exceptional configurational stability with racemization energy barriers higher than 40 kcal mol. Electronic circular dichroism and TD-DFT calculations permit the assignment of the absolute configuration, demonstrating that the sign of optical rotation is not easily related to the or structure. Separated enantiomers show circularly polarized luminescence with high dissymmetry ratio.

摘要

通过氢键供体/路易斯碱有机催化方法，从硫芳基 - 邻苯二甲酰亚胺苯并[]吩噻嗪中获得硫桥连[5]螺旋烯。报道了使用(1)-(-)-樟脑酸作为手性助剂或手性固定相高效液相色谱法拆分[5]螺旋烯。硫桥连[5]螺旋烯表现出异常的构型稳定性，外消旋化能垒高于40千卡/摩尔。电子圆二色性和含时密度泛函理论计算允许确定绝对构型，表明旋光符号与R或S结构不容易相关。分离出的对映体显示出具有高不对称比的圆偏振发光。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4523/11393524/0ce1357811eb/d4ob00979g-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4523/11393524/38ee209292f3/d4ob00979g-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4523/11393524/c2fc3da325fa/d4ob00979g-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4523/11393524/5ed31e3898c0/d4ob00979g-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4523/11393524/beab3993c8dc/d4ob00979g-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4523/11393524/53aabc43b623/d4ob00979g-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4523/11393524/7471bf8a5833/d4ob00979g-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4523/11393524/0ce1357811eb/d4ob00979g-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4523/11393524/38ee209292f3/d4ob00979g-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4523/11393524/c2fc3da325fa/d4ob00979g-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4523/11393524/5ed31e3898c0/d4ob00979g-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4523/11393524/beab3993c8dc/d4ob00979g-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4523/11393524/53aabc43b623/d4ob00979g-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4523/11393524/7471bf8a5833/d4ob00979g-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4523/11393524/0ce1357811eb/d4ob00979g-f4.jpg

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