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Highly Enantioselective [3+3] Cycloaddition of Aromatic Azomethine Imines with Cyclopropanes Directed by π–π Stacking Interactions
Author(s) -
Zhou YouYun,
Li Jun,
Ling Lin,
Liao SaiHu,
Sun XiuLi,
Li YuXue,
Wang LiJia,
Tang Yong
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201207576
Subject(s) - enantioselective synthesis , stacking , cycloaddition , stereoselectivity , chemistry , computer science , combinatorial chemistry , catalysis , aromaticity , stereochemistry , computational chemistry , organic chemistry , molecule
Designing armory : The side‐arm‐modified In‐TOX/Ni II complex was identified as a highly efficient and stereoselective catalyst for the [3+3] cycloaddition of aromatic azomethine imines with cyclopropanes (see picture). Density functional calculations and control experiments revealed that the directing effect of the side arm through π interactions is crucial to the stereochemical control.