Open AccessDiastereoselective synthesis of chiral 1,3-cyclohexadienals
Author(s) -
Aitor Urosa,
Ignacio E. Tobal,
Ángela P. de la Granja,
M. Carmen Capitán,
Rosalina F. Moro,
Isidro S. Marcos,
Narciso M. Garrido,
Francisca Sanz,
Emilio Calle,
David Dı́ez
Publication year - 2018
Publication title -
plos one
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.99
H-Index - 332
ISSN - 1932-6203
DOI - 10.1371/journal.pone.0192113
Subject(s) - aldehyde , enantioselective synthesis , chemistry , combinatorial chemistry , stereoisomerism , chirality (physics) , stereochemistry , organic chemistry , catalysis , physics , chiral perturbation theory , pion , particle physics , nambu–jona lasinio model
A novel approach to the production of chiral 1,3-cyclohexadienals has been developed. The organocatalysed asymmetric reaction of different β-disubstituted-α,β-unsaturated aldehydes with a chiral α,β-unsaturated aldehyde in the presence of a Jørgensen-Hayashi organocatalyst provides easy and stereocontrolled access to the cyclohexadienal backbone. This method allows for the synthesis of potential photoprotective chiral 1,3-cyclohexadienals and extra extended conjugation compounds in a simple manner.