Atroposelective Formal [2 + 5] Macrocyclization Synthesis for a Novel All-Hydrocarbon Cyclo[7] Meta-Benzene Macrocycle-Reference-Cited by-同舟云学术

Atroposelective Formal [2 + 5] Macrocyclization Synthesis for a Novel All-Hydrocarbon Cyclo[7] Meta-Benzene Macrocycle

Published:2024-07-17 Issue:14 Volume:29 Page:3363
ISSN:1420-3049
Container-title:Molecules
language:en
Short-container-title:Molecules

Author:

Gao Chao¹^ORCID,Li Hongchen²,Zhao Jing¹^ORCID,Bu Lulu¹,Sun Mei¹^ORCID,Wang Jingrui¹,Tao Gang¹,Wang Longde¹,Li Li¹,Wen Guilin¹,Hu Yunhu¹

Affiliation:

1. School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China

2. CNOOC Institute of Chemicals & Advanced Materials, Beijing 102209, China

Abstract

A novel axially chiral all-hydrocarbon cyclo[7] (1,3-(4,6-dimethyl)benzene (CDMB-7) was designed and synthesized using atroposelective[2 + 5] cyclization through Suzuki–Miyaura coupling. CDMB-7 adopts an irregular bowl-like shape with C2 symmetry and exhibits two diastereoisomers in its crystallographic structure. The conformational isomers of CDMB-7 racemates remain stable at high temperatures (393 K). High-performance liquid chromatography (HPLC) confirmed that a single chiral isomer will spontaneously undergo racemization within 30 min at room temperature. This finding opens up possibilities for achieving adaptive chirality in all-hydrocarbon cyclo[7] m-benzene macrocycles.

Funder

the key Natural Science Foundation of Anhui Province

Science and Technology Planning Project of Huainan

Publisher

MDPI AG

Link

https://www.mdpi.com/1420-3049/29/14/3363/pdf

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