Excited-State Dynamics Achieved Ultimate Stereocontrol of Photocyclodimerization of Anthracenecarboxylates on a Glucose Scaffold

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• 作者：Gaku Fukuhara ; Kazuhiro Iida ; Yuko Kawanami ; Hidekazu Tanaka ; Tadashi Mori ; Yoshihisa Inoue
• 刊名：Journal of the American Chemical Society
• 出版年：2015
• 出版时间：December 2, 2015
• 年：2015
• 卷：137
• 期：47
• 页码：15007-15014
• 全文大小：500K
• ISSN：1520-5126

文摘

Near-perfect stereoselectivity was attained in the diastereodifferentiating [4 + 4] photocyclodimerization of 2-anthracenecarboxylates tethered to a glucose scaffold not by thermodynamically tuning the conformer equilibrium in the ground state but by kinetically controlling the conformer dynamics and reactivity in the excited state, which enabled us, after removal of the scaffold, to obtain a single enantiomer of chiral anti-head-to-head-cyclodimer in >99% optical and 96% chemical yield from an ensemble of four precursor conformers.