A remarkable stereoselectivity switching upon solid-state versus solution-phase enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by native and 3,6-anhydro-γ-cyclodextrins

Cheng Yang; Masaki Nishijima; Asao Nakamura; Tadashi Mori; Takehiko Wada; Yoshihisa Inoue

doi:10.1016/j.tetlet.2007.04.104

A remarkable stereoselectivity switching upon solid-state versus solution-phase enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by native and 3,6-anhydro-γ-cyclodextrins

Cheng Yang, Masaki Nishijima, Asao Nakamura, Tadashi Mori, Takehiko Wada, Yoshihisa Inoue

IMRAM - Division of Organic- and Biomaterials Research

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

31 Citations (Scopus)

Abstract

The enantiodifferentiating [4+4] photocyclodimerization of anthracenecarboxylic acid (AC) mediated by native, mono- and di-3,6-anhydro-γ-cyclodextrins was investigated in both aqueous solution and solid-state. The solid-state photolyses gave inherently disfavored head-to-head photodimers in much higher chemical and optical yields than in the aqueous solution.

Original language	English
Pages (from-to)	4357-4360
Number of pages	4
Journal	Tetrahedron Letters
Volume	48
Issue number	25
DOIs	https://doi.org/10.1016/j.tetlet.2007.04.104
Publication status	Published - 2007 Jun 18

Keywords

3,6-Anhydro-γ-cyclodextrin
Anthracenecarboxylic acid
Photocyclodimerization
Solid-state

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Yang, C., Nishijima, M., Nakamura, A., Mori, T., Wada, T., & Inoue, Y. (2007). A remarkable stereoselectivity switching upon solid-state versus solution-phase enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by native and 3,6-anhydro-γ-cyclodextrins. Tetrahedron Letters, 48(25), 4357-4360. https://doi.org/10.1016/j.tetlet.2007.04.104

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title = "A remarkable stereoselectivity switching upon solid-state versus solution-phase enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by native and 3,6-anhydro-γ-cyclodextrins",

abstract = "The enantiodifferentiating [4+4] photocyclodimerization of anthracenecarboxylic acid (AC) mediated by native, mono- and di-3,6-anhydro-γ-cyclodextrins was investigated in both aqueous solution and solid-state. The solid-state photolyses gave inherently disfavored head-to-head photodimers in much higher chemical and optical yields than in the aqueous solution.",

keywords = "3,6-Anhydro-γ-cyclodextrin, Anthracenecarboxylic acid, Photocyclodimerization, Solid-state",

author = "Cheng Yang and Masaki Nishijima and Asao Nakamura and Tadashi Mori and Takehiko Wada and Yoshihisa Inoue",

year = "2007",

month = jun,

day = "18",

doi = "10.1016/j.tetlet.2007.04.104",

language = "English",

volume = "48",

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Yang, C, Nishijima, M, Nakamura, A, Mori, T, Wada, T & Inoue, Y 2007, 'A remarkable stereoselectivity switching upon solid-state versus solution-phase enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by native and 3,6-anhydro-γ-cyclodextrins', Tetrahedron Letters, vol. 48, no. 25, pp. 4357-4360. https://doi.org/10.1016/j.tetlet.2007.04.104

A remarkable stereoselectivity switching upon solid-state versus solution-phase enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by native and 3,6-anhydro-γ-cyclodextrins. / Yang, Cheng; Nishijima, Masaki; Nakamura, Asao et al.
In: Tetrahedron Letters, Vol. 48, No. 25, 18.06.2007, p. 4357-4360.

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

TY - JOUR

T1 - A remarkable stereoselectivity switching upon solid-state versus solution-phase enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by native and 3,6-anhydro-γ-cyclodextrins

AU - Yang, Cheng

AU - Nishijima, Masaki

AU - Nakamura, Asao

AU - Mori, Tadashi

AU - Wada, Takehiko

AU - Inoue, Yoshihisa

PY - 2007/6/18

Y1 - 2007/6/18

N2 - The enantiodifferentiating [4+4] photocyclodimerization of anthracenecarboxylic acid (AC) mediated by native, mono- and di-3,6-anhydro-γ-cyclodextrins was investigated in both aqueous solution and solid-state. The solid-state photolyses gave inherently disfavored head-to-head photodimers in much higher chemical and optical yields than in the aqueous solution.

AB - The enantiodifferentiating [4+4] photocyclodimerization of anthracenecarboxylic acid (AC) mediated by native, mono- and di-3,6-anhydro-γ-cyclodextrins was investigated in both aqueous solution and solid-state. The solid-state photolyses gave inherently disfavored head-to-head photodimers in much higher chemical and optical yields than in the aqueous solution.

KW - 3,6-Anhydro-γ-cyclodextrin

KW - Anthracenecarboxylic acid

KW - Photocyclodimerization

KW - Solid-state

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DO - 10.1016/j.tetlet.2007.04.104

M3 - Article

AN - SCOPUS:34248681829

SN - 0040-4039

VL - 48

SP - 4357

EP - 4360

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 25

ER -

A remarkable stereoselectivity switching upon solid-state versus solution-phase enantiodifferentiating photocyclodimerization of 2-anthracenecarboxylic acid mediated by native and 3,6-anhydro-γ-cyclodextrins

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Keywords

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