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Synthesis of [7]Helicene Enantiomers and Exploratory Study of Their Conversion into Helically Chiral Iodoarenes and Iodanes
Author(s) -
Antien Kevin,
Pouységu Laurent,
Deffieux Denis,
Massip Stéphane,
Peixoto Philippe A.,
Quideau Stéphane
Publication year - 2019
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.201805761
Subject(s) - helicene , enantiomer , tartaric acid , chemistry , reagent , combinatorial chemistry , ether , organic chemistry , chiral derivatizing agent , chiral column chromatography , molecule , citric acid
The facile and convenient preparation of both enantiomers of a [7]helicene scaffold from inexpensive ( l )‐(+)‐tartaric acid and 4‐methylstyrene is described. These helical structures were transformed into bis‐iodinated ether derivatives in order to explore their potential as precursors of novel chiral organoiodane reagents or as iodoarene pre‐catalysts. Promising results were obtained in hydroxylative phenol dearomatization/[4+2] cycloaddition cascade and dearomative spirolactonization reactions with encouraging enantiomeric excesses.