Enantiodifferentiating Photocyclodimerization of 2‑Anthracenecarboxylic Acid via Competitive Binary/Ternary Hydrogen-Bonded Complexes with 4‑Benzamidoprolinol

Enantiodifferentiating Photocyclodimerization of 2‑Anthracenecarboxylic Acid via Competitive Binary/Ternary Hydrogen-Bonded Complexes with 4‑Benzamidoprolinol

Circular dichroism (CD) spectral examinations at various host/guest ratios revealed that 2-anthracenecarboxylic acid (AC) forms not only 1:1 but also novel 2:1 hydrogen-bonded/π-stacked complexes with a chiral 4-benzamidoprolinol template (TKS159). The 2:1 complexation is a minor process but causes...

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Veröffentlicht in:Organic letters 2012-09, Vol.14 (18), p.4962-4965
Hauptverfasser: Kawanami, Yuko, Katsumata, Shin-ya, Mizoguchi, Jun-ichi, Nishijima, Masaki, Fukuhara, Gaku, Yang, Cheng, Mori, Tadashi, Inoue, Yoshihisa
Format: Artikel
Sprache:eng
Schlagworte:
Anthracenes - chemistry
Carboxylic Acids - chemistry
Circular Dichroism
Dimerization
Hydrogen Bonding
Molecular Structure
Photochemical Processes
Pyrrolidines - chemistry
Stereoisomerism
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Zusammenfassung:Circular dichroism (CD) spectral examinations at various host/guest ratios revealed that 2-anthracenecarboxylic acid (AC) forms not only 1:1 but also novel 2:1 hydrogen-bonded/π-stacked complexes with a chiral 4-benzamidoprolinol template (TKS159). The 2:1 complexation is a minor process but causes significant CD spectral changes as a consequence of the exciton coupling interaction of two AC chromophores and greatly accelerates the head-to-head photocyclodimerization to significantly affect the stereochemical outcomes.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol3023402