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

被引：29

作者：

Fukuhara, Gaku ^{[1
]}

Iida, Kazuhiro ^{[1
]}

Kawanami, Yuko ^{[1
]}

Tanaka, Hidekazu ^{[1
]}

Mori, Tadashi ^{[1
]}

Inoue, Yoshihisa ^{[1
]}

机构：

[1] Osaka Univ, Dept Appl Chem, Suita, Osaka 5650871, Japan

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 47期

关键词：

PHOTOCHEMICAL-REACTIONS; CHIRAL INDUCTION; 2+2 PHOTOCYCLOADDITION; ASYMMETRIC INDUCTION; DIASTEREODIFFERENTIATING PHOTOCYCLODIMERIZATION; CIRCULAR-DICHROISM; CONFORMATIONAL-ANALYSIS; DIASTEREOSELECTIVITY; ANTHRACENE; 2-ANTHRACENECARBOXYLATE;

D O I：

10.1021/jacs.5b09775

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

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页码：15007 / 15014

页数：8

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