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Title

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

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Gavrilov, Konstantin N.
Benetskiy, Eduard B.
Grishina, Tatiana B.
Rastorguev, Eugenie A.
Maksimova, Marina G.
Zheglov, Sergey V.
Davankov, Vadim A.
Schäffner, Benjamin
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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
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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. https://archive-ouverte.unige.ch/unige:8234

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Deposited on : 2010-06-21

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