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

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 an...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2015-12, Vol.137 (47), p.15007-15014
Main Authors: Fukuhara, Gaku, Iida, Kazuhiro, Kawanami, Yuko, Tanaka, Hidekazu, Mori, Tadashi, Inoue, Yoshihisa
Format: Article
Language:English
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.5b09775