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

Chao Gao; Hongchen Li; Jing Zhao; Lulu Bu; Mei Sun; Jingrui Wang; Gang Tao; Longde Wang; Li Li; Guilin Wen; Yunhu Hu

doi:10.3390/molecules29143363

Molecules (Jul 2024)

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

Chao Gao,
Hongchen Li,
Jing Zhao,
Lulu Bu,
Mei Sun,
Jingrui Wang,
Gang Tao,
Longde Wang,
Li Li,
Guilin Wen,
Yunhu Hu

Affiliations

Chao Gao: School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China
Hongchen Li: CNOOC Institute of Chemicals & Advanced Materials, Beijing 102209, China
Jing Zhao: School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China
Lulu Bu: School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China
Mei Sun: School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China
Jingrui Wang: School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China
Gang Tao: School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China
Longde Wang: School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China
Li Li: School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China
Guilin Wen: School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China
Yunhu Hu: School of Chemistry and Materials Engineering, Huainan Normal University, Huainan 232038, China

DOI: https://doi.org/10.3390/molecules29143363
Journal volume & issue: Vol. 29, no. 14
p. 3363

Abstract

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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.

Published in Molecules

ISSN: 1420-3049 (Online)
Publisher: MDPI AG
Country of publisher: Switzerland
LCC subjects: Science: Chemistry: Organic chemistry
Website: http://www.mdpi.com/journal/molecules

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