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 | Zendy

Castro Edison | Zendy; Azmani Khalid | Zendy; Garcia Andrea Hernandez | Zendy; Aghabali Amineh | Zendy; Liu Shuming | Zendy; MettaMagana Alejandro J. | Zendy; Olmstead Marilyn M. | Zendy; RodríguezFortea Antonio | Zendy; Poblet Josep M. | Zendy; Echegoyen Luis | Zendy

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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.

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