UNIGE document Scientific Article
previous document  unige:8234  next document
add to browser collection

Bulky P*-Chirogenic Diazaphospholidines as monodentate ligands for asymmetric catalysis

Gavrilov, Konstantin N.
Benetskiy, Eduard B.
Grishina, Tatiana B.
Rastorguev, Eugenie A.
Maksimova, Marina G.
Zheglov, Sergey V.
Davankov, Vadim A.
Schäffner, Benjamin
show hidden authors show all authors [1 - 12]
Published in European Journal of Organic Chemistry. 2009, no. 23, p. 3923-3929
Abstract A series of easily prepared bulky P*-chiral diamidophosphites based on (2R,5S)-3-phenyl-1,3-diaza-2-phosphabicyclo[3.3.0]octane and (2R,5S)-3-(p-bromophenyl)-1,3-diaza-2-phosphabicyclo[3.3.0]octane backbones have been designed and developed. Ligands of this type exhibited high enantioselectivities in Pd-catalysed allylic substitution reactions of (E)-1,3-diphenylallyl acetate with NaSO2pTol (up to 87 % ee), CH2(CO2Me)2 (up to 92 % ee), (C3H7)2NH (up to 93 % ee) and (CH2)4NH (up to 99 % ee). These novel stereoselectors have also been successfully employed in Rh-catalysed asymmetric hydrogenations of dimethyl itaconate (up to 76 % ee), methyl (Z)-2-acetamido-3-phenylacrylate (up to 73 % ee) and methyl 2-acetamidoacrylate (up to 98 % ee). Cu-catalysed conjugate addition of diethylzinc to cyclohexenone leads to a maximum of 70 % ee with quantitative conversion.
Keywords Asymmetric catalysisP li­gandsHydrogenationAllylationConjugate addition
Full text
Article (Published version) - document accessible for UNIGE members only Limited access to UNIGE
(ISO format)
GAVRILOV, Konstantin N. et al. Bulky P*-Chirogenic Diazaphospholidines as monodentate ligands for asymmetric catalysis. In: European Journal of Organic Chemistry, 2009, n° 23, p. 3923-3929. doi: 10.1002/ejoc.200900058 https://archive-ouverte.unige.ch/unige:8234

400 hits

0 download


Deposited on : 2010-06-21

Export document
Format :
Citation style :