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

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• 作者：Yuko Kawanami ; Shin-ya Katsumata ; Jun-ichi Mizoguchi ; Masaki Nishijima ; Gaku Fukuhara ; Cheng Yang ; Tadashi Mori ; Yoshihisa Inoue
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：September 21, 2012
• 年：2012
• 卷：14
• 期：18
• 页码：4962-4965
• 全文大小：233K
• 年卷期：v.14,no.18(September 21, 2012)
• ISSN：1523-7052

文摘

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/蟺-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.