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Unusual C 2h ‐Symmetric trans‐ 1‐(Bis‐pyrrolidine)‐tetra‐malonate Hexa‐Adducts of C 60 : The Unexpected Regio‐ and Stereocontrol Mediated by Malonate–Pyrrolidine Interaction
Author(s) -
Castro Edison,
Azmani Khalid,
Garcia Andrea Hernandez,
Aghabali Amineh,
Liu Shuming,
MettaMagana Alejandro J.,
Olmstead Marilyn M.,
RodríguezFortea Antonio,
Poblet Josep M.,
Echegoyen Luis
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201702866
Subject(s) - pyrrolidine , malonate , chemistry , hexa , stereoselectivity , tetra , adduct , cycloaddition , stereochemistry , dimethyl malonate , medicinal chemistry , enantioselective synthesis , organic chemistry , catalysis
A totally unanticipated regio‐ and stereoisomerically pure C 2h ‐symmetric trans‐ 1‐(bis‐pyrrolidine)‐tetra‐malonate hexa ‐ adduct of C 60 was obtained via a topologically controlled method, followed by a 1,3‐dipolar cycloaddition reaction. The structures of the products were elucidated by 1 H and 13 C NMR and by X‐ray crystallography. The unexpected regio‐ and stereoselectivity observed, supported by theoretical calculations, was found to be a consequence of malonate–pyrrolidine interactions.