Premium
Hierarchical Selectivity in Fullerenes: Site‐, Regio‐, Diastereo‐, and Enantiocontrol of the 1,3‐Dipolar Cycloaddition to C 70
Author(s) -
Maroto Enrique E.,
de Cózar Abel,
Filippone Salvatore,
MartínDomenech Ángel,
Suarez Margarita,
Cossío Fernando P.,
Martín Nazario
Publication year - 2011
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.201101246
Subject(s) - regioselectivity , cycloaddition , enantioselective synthesis , fullerene , nucleophile , electrophile , enantiomer , chemistry , selectivity , computational chemistry , stereochemistry , combinatorial chemistry , organic chemistry , catalysis
Make your choice of stereochemistry : The first enantioselective cycloaddition of N‐metalated azomethine ylides to the C 70 molecule affords both pyrrolidino[70]fullerene enantiomers, with ee values over 90 %, depending on the chiral metal complex used (see picture). The high site‐ and regioselectivity observed has been accounted for by the nucleophilic and electrophilic Fukui indexes determined by theoretical calculations.