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Volume 25
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Article

VCD Analysis of Axial Chirality in Synthetic Stereoisomeric Biaryl-Type bis-Isochroman Heterodimers with Isolated Blocks of Central and Axial Chirality †

by
Zoltán Czenke
1,2,
Attila Mándi
1,
Sándor Balázs Király
1,
Attila Kiss-Szikszai
1,
Anita Kónya-Ábrahám
1,
Anna Kurucz-Szabados
1,2,
Krisztián Cserepes
1,2,
Attila Bényei
3,
Changsheng Zhang
4,
Máté Kicsák
1,* and
Tibor Kurtán
1,*
1
Department of Organic Chemistry, University of Debrecen, P. O. Box 400, 4002 Debrecen, Hungary
2
Doctoral School of Chemistry, University of Debrecen, Egyetem tér 1., 4032 Debrecen, Hungary
3
Department of Physical Chemistry, University of Debrecen, Egyetem tér 1., 4032 Debrecen, Hungary
4
Key Laboratory of Tropical Marine Bio-Resources and Ecology, Guangdong Key Laboratory of Marine Materia Medica, Institutions of South China Sea Ecology and Environmental Engineering, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China
*
Authors to whom correspondence should be addressed.
†
Dedicated to the anniversary of professor György Keglevich.
Int. J. Mol. Sci. 2024, 25(17), 9657; https://doi.org/10.3390/ijms25179657
Submission received: 30 July 2024 / Revised: 26 August 2024 / Accepted: 29 August 2024 / Published: 6 September 2024
(This article belongs to the Special Issue Recent Trends in Stereoselective Synthesis and Chiral Catalysis)
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Abstract

Optically active heterodimeric 5,5′-linked bis-isochromans, containing a stereogenic ortho-trisubstituted biaryl axis and up to four chirality centers, were synthesized stereoselectively by using a Suzuki–Miyaura biaryl coupling reaction of optically active isochroman and 1-arylpropan-2-ol derivatives, providing the first access to synthetic biaryl-type isochroman dimers. Enantiomeric pairs and stereoisomers up to seven derivatives were prepared with four different substitution patterns, which enabled us to test how OR, ECD, and VCD measurements and DFT calculations can be used to determine parallel central and axial chirality elements in three isolated blocks of chirality. In contrast to natural penicisteckins A–D and related biaryls, the ECD spectra and OR data of (aS) and (aR) atropodiastereomers did not reflect the opposite axial chirality, but they were characteristic of the central chirality. The atropodiastereomers showed consistently near-mirror-image VCD curves, allowing the determination of axial chirality with the aid of DFT calculation or by comparison of characteristic VCD transitions.
Keywords: stereogenic biaryl axis; stereoisomeric bis-isochromans; isolated blocks of chirality; VCD; ECD stereogenic biaryl axis; stereoisomeric bis-isochromans; isolated blocks of chirality; VCD; ECD
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MDPI and ACS Style

Czenke, Z.; Mándi, A.; Király, S.B.; Kiss-Szikszai, A.; Kónya-Ábrahám, A.; Kurucz-Szabados, A.; Cserepes, K.; Bényei, A.; Zhang, C.; Kicsák, M.; et al. VCD Analysis of Axial Chirality in Synthetic Stereoisomeric Biaryl-Type bis-Isochroman Heterodimers with Isolated Blocks of Central and Axial Chirality. Int. J. Mol. Sci. 2024, 25, 9657. https://doi.org/10.3390/ijms25179657

AMA Style

Czenke Z, Mándi A, Király SB, Kiss-Szikszai A, Kónya-Ábrahám A, Kurucz-Szabados A, Cserepes K, Bényei A, Zhang C, Kicsák M, et al. VCD Analysis of Axial Chirality in Synthetic Stereoisomeric Biaryl-Type bis-Isochroman Heterodimers with Isolated Blocks of Central and Axial Chirality. International Journal of Molecular Sciences. 2024; 25(17):9657. https://doi.org/10.3390/ijms25179657

Chicago/Turabian Style

Czenke, Zoltán, Attila Mándi, Sándor Balázs Király, Attila Kiss-Szikszai, Anita Kónya-Ábrahám, Anna Kurucz-Szabados, Krisztián Cserepes, Attila Bényei, Changsheng Zhang, Máté Kicsák, and et al. 2024. "VCD Analysis of Axial Chirality in Synthetic Stereoisomeric Biaryl-Type bis-Isochroman Heterodimers with Isolated Blocks of Central and Axial Chirality" International Journal of Molecular Sciences 25, no. 17: 9657. https://doi.org/10.3390/ijms25179657

APA Style

Czenke, Z., Mándi, A., Király, S. B., Kiss-Szikszai, A., Kónya-Ábrahám, A., Kurucz-Szabados, A., Cserepes, K., Bényei, A., Zhang, C., Kicsák, M., & Kurtán, T. (2024). VCD Analysis of Axial Chirality in Synthetic Stereoisomeric Biaryl-Type bis-Isochroman Heterodimers with Isolated Blocks of Central and Axial Chirality. International Journal of Molecular Sciences, 25(17), 9657. https://doi.org/10.3390/ijms25179657

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