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Sequential Tether‐Directed Synthesis of Pentakis‐Adducts of C 60 with a Mixed [3:2] Octahedral Addition Pattern
Author(s) -
Maxouti Katerina L.,
Hirsch Andreas
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800091
Subject(s) - adduct , chemistry , malonate , enantiomer , octahedron , cyclopropanation , fullerene , derivative (finance) , surface modification , stereochemistry , sequence (biology) , organic chemistry , crystal structure , catalysis , biochemistry , financial economics , economics
The design of a novel concept for the synthesis of [3:2] pentakis‐adducts of fullerene C 60 is presented. A sequential tether‐directed, remote functionalization approach is introduced for the construction of the pentakis‐adducts. This fullerene derivative embellished with two different addends in two different directions can be considered as a valuable tecton for further functionalization. The stepwise cyclopropanation of C 60 with a macrocyclic tris‐malonate and a bis(β‐keto ester) yielded the corresponding pentakis‐adduct with an incomplete octahedral addition pattern. This reaction sequence gave access to two pairs of enantiomers that were easily separated by column chromatography on an achiral stationary phase and subsequently characterized.