Planar-to-planar chirality transfer in the excited state. Enantiodifferentiating photoisomerization of cyclooctenes sensitized by planar-chiral paracyclophane

Ryo Maeda; Takehiko Wada; Tadashi Mori; Shigeyuki Kono; Nobuhiro Kanomata; Yoshihisa Inoue

doi:10.1021/ja203781f

Planar-to-planar chirality transfer in the excited state. Enantiodifferentiating photoisomerization of cyclooctenes sensitized by planar-chiral paracyclophane

Ryo Maeda, Takehiko Wada, Tadashi Mori, Shigeyuki Kono, Nobuhiro Kanomata^*, Yoshihisa Inoue

^*Corresponding author for this work

School of Advanced Science and Engineering

Research output: Contribution to journal › Article › peer-review

38 Citations (Scopus)

Abstract

Photochemical planar-to-planar chirality transfer was effected by using (R)-[10]paracyclophane-12-carboxylates as a planar-chiral sensitizer and (Z)-cyclooctene and (Z,Z)-1,5-cyclooctadiene as prochiral substrates to give a planar-chiral (E)- and (E,Z)-isomer in up to 44% and 87% enantiomeric excess, respectively, the latter of which being the highest ever reported for a sensitized photochirogenic reaction.

Original language	English
Pages (from-to)	10379-10381
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	133
Issue number	27
DOIs	https://doi.org/10.1021/ja203781f
Publication status	Published - 2011 Jul 13

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja203781f

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Planar-to-planar chirality transfer in the excited state. Enantiodifferentiating photoisomerization of cyclooctenes sensitized by planar-chiral paracyclophane. / Maeda, Ryo; Wada, Takehiko; Mori, Tadashi et al.
In: Journal of the American Chemical Society, Vol. 133, No. 27, 13.07.2011, p. 10379-10381.

Research output: Contribution to journal › Article › peer-review

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abstract = "Photochemical planar-to-planar chirality transfer was effected by using (R)-[10]paracyclophane-12-carboxylates as a planar-chiral sensitizer and (Z)-cyclooctene and (Z,Z)-1,5-cyclooctadiene as prochiral substrates to give a planar-chiral (E)- and (E,Z)-isomer in up to 44% and 87% enantiomeric excess, respectively, the latter of which being the highest ever reported for a sensitized photochirogenic reaction.",

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AU - Mori, Tadashi

AU - Kono, Shigeyuki

AU - Kanomata, Nobuhiro

AU - Inoue, Yoshihisa

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Planar-to-planar chirality transfer in the excited state. Enantiodifferentiating photoisomerization of cyclooctenes sensitized by planar-chiral paracyclophane

Abstract

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