Scope and limitations of absolute configuration determination of allenic natural products using the C=C=C stretching VCD signal

Taniguchi, Tohru; Mutmainah; Takimoto, Shu et al.

Organic & biomolecular chemistry, 2023, 21(3), 569-574

Permalink : https://hdl.handle.net/2115/91069

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アクセス権
open access
URI
https://hdl.handle.net/2115/91069
タイトル
Scope and limitations of absolute configuration determination of allenic natural products using the C=C=C stretching VCD signal
著者
Taniguchi, Tohru ; Mutmainah ; Takimoto, Shu ; Suzuki, Takahiro ; Watanabe, Soichiro ; Matsuda, Fuyuhiko ; Umezawa, Taiki ; Monde, Kenji
e-Rad_Researcher
00587123
著者名
Taniguchi, Tohru
著者名
Mutmainah
著者名
Takimoto, Shu
著者名
Suzuki, Takahiro
著者名
Watanabe, Soichiro
著者名
Matsuda, Fuyuhiko
著者名
Umezawa, Taiki
e-Rad_Researcher
40210207
著者名
Monde, Kenji
言語
英語
発行日
2023-01-21
出版者
Royal Society of Chemistry
収録物名
Organic & biomolecular chemistry
巻(号)
21(3)
ページ
569-574
抄録
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.
資源タイプ
学術雑誌論文
出版タイプ
Accepted Manuscript
PISSN
1477-0520
関連情報 (isVersionOf)
出版社版DOI
https://doi.org/10.1039/d2ob01520j