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Hokkaido University Collection of Scholarly and Academic Papers >
Graduate School of Life Science / Faculty of Advanced Life Science >
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Scope and limitations of absolute configuration determination of allenic natural products using the C=C=C stretching VCD signal
| Title: | Scope and limitations of absolute configuration determination of allenic natural products using the C=C=C stretching VCD signal |
| Authors: | Taniguchi, Tohru Browse this author →KAKEN DB | | Mutmainah Browse this author | | Takimoto, Shu Browse this author | | Suzuki, Takahiro Browse this author | | Watanabe, Soichiro Browse this author | | Matsuda, Fuyuhiko Browse this author | | Umezawa, Taiki Browse this author | | Monde, Kenji Browse this author →KAKEN DB |
| Issue Date: | 21-Jan-2023 |
| Publisher: | Royal Society of Chemistry |
| Journal Title: | Organic & biomolecular chemistry |
| Volume: | 21 |
| Issue: | 3 |
| Start Page: | 569 |
| End Page: | 574 |
| Publisher DOI: | 10.1039/d2ob01520j |
| Abstract: | The allene functional group in natural products isolated so far exists in a non-racemic form, but its axial chirality is difficult to elucidate. Allenes exhibit a characteristic antisymmetric C=C=C stretching mode at around 1950 cm(-1), and their VCD properties have not been studied in detail. This work, for the first time, applied VCD spectroscopy to allenic natural products and allenic molecules with other asymmetric centers focusing on the antisymmetric C=C=C stretching mode. This vibrational mode yielded a negligibly weak VCD signal for several molecules, but in the presence of electron-withdrawing and/or conjugating substituents, it generated a stronger one. Its sign was found to be influenced by the nature of substituents. These findings should deepen the understanding of the VCD properties of the allene functional group and should be useful for future studies of chiral allenes. |
| Type: | article (author version) |
| URI: | http://hdl.handle.net/2115/91069 |
| Appears in Collections: | 生命科学院・先端生命科学研究院 (Graduate School of Life Science / Faculty of Advanced Life Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)
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Submitter: 谷口 透
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